1958:
2178:
1875:
2200:
2002:
466:
1583:
594:
2156:
1346:
2129:
1293:
1322:
1919:
2046:
1239:
2102:
1395:
1268:
2274:
1980:
1809:
263:
2024:
1554:
365:
717:
1897:
1370:
563:
229:
1853:
1765:
626:
1831:
1487:
1459:
1431:
1787:
498:
1680:
1608:
331:
297:
658:
532:
433:
399:
1130:
1152:). Crocetin is a 20-carbon chain dicarboxylic acid which is a diterpenoid and can be considered as a carotenoid. It was the first plant carotenoid to be recognized as early as 1818 while the history of saffron cultivation reaches back more than 3,000 years. The major active ingredient of saffron is the yellow pigment
1109:, deep-sea marine hydrothermal systems and high-temperature marine and continental oil fields. It was shown that about 10% of their lipid fraction were symmetrical C30 to C34 diabolic acids. The C30 (13,14-dimethyloctacosanedioic acid) and C32 (15,16-dimethyltriacontanedioic acid) diabolic acids have been described in
2235:
Dicarboxylic acids are crystalline solids. Solubility in water and melting point of the α,ω- compounds progress in a series as the carbon chains become longer with alternating between odd and even numbers of carbon atoms, so that for even numbers of carbon atoms the melting point is higher than for
919:, cosmetics, candles, etc. It is also used in the synthesis of polyamide, as nylon, and of alkyd resins. An isomer, isosebacic acid, has several applications in the manufacture of vinyl resin plasticizers, extrusion plastics, adhesives, ester lubricants, polyesters, polyurethane resins and
2305:
As for monofunctional carboxylic acids, derivatives of the same types exist; however, there is the added complication that one or both of the carboxylic groups could be altered. If only one is changed then the derivative is termed "acid", and if both ends are altered it is called "normal".
1125:
Biphytanic diacids are present in geological sediments and are considered as tracers of past anaerobic oxidation of methane. Several forms without or with one or two pentacyclic rings have been detected in
Cenozoic seep limestones. These lipids may be unrecognized metabolites from Archaea.
2247:
The dicarboxylic acids, especially the small and linear ones, can be used as crosslinking reagents. Dicarboxylic acids where the carboxylic groups are separated by none or one carbon atom decompose when they are heated to give off carbon dioxide and leave behind a monocarboxylic acid.
3307:
Nishimura, Hiroshi; Murayama, Kyoko; Watanabe, Takahito; Honda, Yoichi; Watanabe, Takashi (June 2009). "Absolute configuration of ceriporic acids, the iron redox-silencing metabolites produced by a selective lignin-degrading fungus, Ceriporiopsis subvermispora".
948:
Dodecanedioic acid is used in the production of nylon (nylon-6,12), polyamides, coatings, adhesives, greases, polyesters, dyestuffs, detergents, flame retardants, and fragrances. It is now produced by fermentation of long-chain alkanes with a specific strain of
1623:
Traumatic acid, was among the first biologically active molecules isolated from plant tissues. This dicarboxylic acid was shown to be a potent wound healing agent in plant that stimulates cell division near a wound site, it derives from 18:2 or 18:3 fatty acid
2762:
Huber, Robert; Langworthy, Thomas A.; König, Helmut; Thomm, Michael; Woese, Carl R.; Sleytr, Uwe B.; Stetter, Karl O. (May 1986). "Thermotoga maritima sp. nov. represents a new genus of unique extremely thermophilic eubacteria growing up to 90 °C".
2677:
Longmuir, Kenneth J.; Rossi, Mary E.; Resele-Tiden, Christine (1987). "Determination of monoenoic fatty acid double bond position by permanganate-periodate oxidation followed by high-performance liquid chromatography of carboxylic acid phenacyl esters".
1703:(methylenesuccinic acid) being a metabolite produced by filamentous fungi. Among these compounds, several analogues, called chaetomellic acids with different chain lengths and degrees of unsaturation have been isolated from various species of the lichen
998:
present at vegetal surfaces (outer bark, root epidermis). C16 to C26 α,ω-dioic acids are considered as diagnostic for suberin. With C18:1 and C18:2, their content amount from 24 to 45% of whole suberin. They are present at low levels (< 5%) in plant
2306:
Derivatives include one or both of the carboxylates being converted to their salts, acid chlorides, esters, amides, and anhydrides. In the case of anhydrides or amides, two of the carboxyl groups can come together to form a cyclic compound, for example
1016:
microorganisms specifically contained a large variety of dicarboxylic acids. This is probably the most important difference between these microorganisms and other marine bacteria. Dioic fatty acids from C16 to C22 were found in an hyperthermophilic
1662:
While polyunsaturated fatty acids are unusual in plant cuticles, a diunsaturated dicarboxylic acid has been reported as a component of the surface waxes or polyesters of some plant species. Thus, octadeca-c6,c9-diene-1,18-dioate, a derivative of
1068:
which is further used in saturated fatty acid synthesis. The determination of the dicarboxylic acids generated by permanganate-periodate oxidation of monoenoic fatty acids was useful to study the position of the double bond in the carbon chain.
2251:
Blanc's Rule says that heating a barium salt of a dicarboxylic acid, or dehydrating it with acetic anhydride will yield a cyclic acid anhydride if the carbon atoms bearing acid groups are in position 1 and (4 or 5). So succinic acid will yield
915:). Thenard isolated this compound from distillation products of beef tallow in 1802. It is produced industrially by alkali fission of castor oil. Sebacic acid and its derivatives have a variety of industrial uses as plasticizers, lubricants,
3197:
Singh, SB; Jayasuriya, H; Silverman, KC; Bonfiglio, CA; Williamson, JM; Lingham, RB (March 2000). "Efficient syntheses, human and yeast farnesyl-protein transferase inhibitory activities of chaetomellic acids and analogues".
3243:
Enoki, Makiko; Watanabe, Takashi; Honda, Yoichi; Kuwahara, Masaaki (2000). "A Novel
Fluorescent Dicarboxylic Acid, (Z)-1,7-Nonadecadiene-2,3-dicarboxylic Acid, Produced by White-Rot Fungus Ceriporiopsis subvermispora".
3271:
Amirta, Rudianto; Fujimori, Kenya; Shirai, Nobuaki; Honda, Yoichi; Watanabe, Takashi (December 2003). "Ceriporic acid C, a hexadecenylitaconate produced by a lignin-degrading fungus, Ceriporiopsis subvermispora".
908:
present on acne-bearing skin. Azelaic acid was identified as a molecule that accumulated at elevated levels in some parts of plants and was shown to be able to enhance the resistance of plants to infections.
1164:) group at each end of the molecule. A simple and specific HPLC-UV method has been developed to quantify the five major biologically active ingredients of saffron, namely the four crocins and crocetin.
986:
A large survey of the dicarboxylic acids present in
Mediterranean nuts revealed unusual components. A total of 26 minor acids (from 2 in pecan to 8% in peanut) were determined: 8 species derived from
1726:), Ceriporiopsis subvermispora. The absolute configuration of ceriporic acids, their stereoselective biosynthetic pathway and the diversity of their metabolites have been discussed in detail.
2923:
Li, Na; Lin, Ge; Kwan, Yiu-Wa; Min, Zhi-Da (July 1999). "Simultaneous quantification of five major biologically active ingredients of saffron by high-performance liquid chromatography".
2240:
tending towards values of ca. 4.5 and 5.5 as the separation between the two carboxylate groups increases. Thus, in an aqueous solution at pH about 7, typical of biological systems, the
3001:
Wiwanitkit V, Soogarun S, Suwansaksri J (2007). "A correlative study on red blood cell parameters and urine trans, trans-muconic acid in subjects with occupational benzene exposure".
1052:
and triundecylin. Although the significance of their biosynthesis remains poorly understood, it was demonstrated that ω-oxidation occurs in rat liver but at a low rate, needs oxygen,
841:
Suberic acid was first produced by nitric acid oxidation of cork (Latin suber). This acid is also produced when castor oil is oxidised. Suberic acid is used in the manufacture of
3158:"Analysis of the aliphatic monomer composition of polyesters associated with Arabidopsis epidermis: occurrence of octadeca-cis-6, cis-9-diene-1,18-dioate as the major component"
2256:. For acids with carboxylic groups at position 1 and 6 this dehydration causes loss of carbon dioxide and water to form a cyclic ketone, for example, adipic acid will form
1116:
Some parent C29 to C32 diacids but with methyl groups on the carbons C-13 and C-16 have been isolated and characterized from the lipids of thermophilic anaerobic bacterium
2849:"A new family of very long chain alpha,omega-dicarboxylic acids is a major structural fatty acyl component of the membrane lipids of Thermoanaerobacter ethanolicus 39E"
2888:
Birgel, Daniel; Elvert, Marcus; Han, Xiqiu; Peckmann, Jörn (January 2008). "13C-depleted biphytanic diacids as tracers of past anaerobic oxidation of methane".
2496:
Dembitsky, Valery M; Goldshlag, Paulina; Srebnik, Morris (April 2002). "Occurrence of dicarboxylic (dioic) acids in some
Mediterranean nuts".
2451:
2715:"A new series of long-chain dicarboxylic acids with vicinal dimethyl branching found as major components of the lipids of Butyrivibrio spp"
2477:
Kroha, Kyle (September 2004). "Industrial biotechnology provides opportunities for commercial production of new long-chain dibasic acids".
2607:
Dembitsky, V. M.; Shkrob, I.; Go, J. V. (2001). "Dicarboxylic and Fatty Acid
Compositions of Cyanobacteria of the Genus Aphanizomenon".
2241:
2354:
Jung, Ho Won; Tschaplinski, Timothy J.; Wang, Lin; Glazebrook, Jane; Greenberg, Jean T. (2009). "Priming in
Systemic Plant Immunity".
2337:
Boy
Cornils, Peter Lappe "Dicarboxylic Acids, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry 2014, Wiley-VCH, Weinheim.
3427:
868:
and in specimens of ointment removed from
Egyptian tombs 5000 years old. Azelaic acid was prepared by oxidation of oleic acid with
2650:
Wada, F.; Usami, M. (1997). "Studies on fatty acid ω-oxidation antiketogenic effect and gluconeogenicity of dicarboxylic acids".
2190:
459:
2523:
Pollard, Mike; Beisson, Fred; Ohlrogge, John B. (3 April 2009). "Building lipid barriers: biosynthesis of cutin and suberin".
769:
Adipic acid, despite its name (in Latin, adipis means fat), is not a normal constituent of natural lipids but is a product of
2800:"Unusual fatty acid compositions of the hyperthermophilic archaeon Pyrococcus furiosus and the bacterium Thermotoga maritima"
2560:"Unusual fatty acid compositions of the hyperthermophilic archaeon Pyrococcus furiosus and the bacterium Thermotoga maritima"
1118:
876:
or by ozonolysis. Azelaic acid is used, as simple esters or branched-chain esters) in the manufacture of plasticizers (for
1957:
3462:
3434:
864:. It was detected among products of rancid fats. Its origin explains for its presence in poorly preserved samples of
3046:"Benzene exposure, assessed by urinary trans,trans-muconic acid, in urban children with elevated blood lead levels"
1909:
1280:
834:, fat) was also first isolated from oxidized oil. Derivatives of pimelic acid are involved in the biosynthesis of
1707:. These molecules were shown to be valuable as basis for the development of anticancer drugs due to their strong
1509:
1140:
is the core compound of crocins (crocetin glycosides) which are the main red pigments of the stigmas of saffron (
1091:, have a chain length depending on the fatty acid used in the culture medium. The most abundant diabolic acid in
1948:
1183:
2285: with: a well sourced, more expansive presentation than that of a 1922 sophomore text. You can help by
856:
Azelaic acid's name stems from the action of nitric acid (azote, nitrogen, or azotic, nitric) oxidation of
2177:
1970:
869:
162:
links gives access to more information on the compounds, including other names, ids, toxicity and safety.
3365:"Development of chitosan membrane using non-toxic crosslinkers for potential wound dressing applications"
1874:
2001:
1060:. It was later shown that this reaction is more important in starving or diabetic animals where 15% of
169:'Oh My Son, Go And Pray Softly And Silently', and also 'Oh my! Such great Apple Pie, sweet as sugar!'.
739:
2897:
2363:
1931:
1148:
1005:
2199:
1691:
Several dicarboxylic acids having an alkyl side chain and an itaconate core have been isolated from
994:, and 18 species with a chain from 5 to 22 carbon atoms. Higher weight acids (>C20) are found in
2014:
1924:
1708:
1110:
1106:
1078:
1023:
465:
1087:, bacteria which participate in the digestion of cellulose in the rumen. These fatty acids, named
680:
3392:
3065:
3026:
2983:
2958:
Farmer, Edward E. (1994). "Fatty acid signalling in plants and their associated microorganisms".
2780:
2632:
2422:
2387:
2319:
2253:
2216:
1887:
1704:
1360:
951:
945:. This diacid is produced on a small commercial scale in Japan for the manufacture of fragrances.
916:
905:
881:
770:
710:
587:
165:
Acids from the two-carbon oxalic acid to the ten-member sebacic acid may be remembered using the
2155:
1345:
1095:
had a 32-carbon chain length. Diabolic acids were also detected in the core lipids of the genus
2128:
975:
is a mixture containing triglycerides of C21, C22 and C23 dicarboxylic acids obtained from the
593:
3384:
3325:
3289:
3215:
3179:
3138:
3083:
3018:
2975:
2940:
2870:
2829:
2744:
2695:
2624:
2589:
2540:
2447:
2441:
2379:
2141:
1723:
1642:
of benzene in humans. The determination of its concentration in urine is therefore used as a
1321:
1013:
960:
814:
60:
40:
20:
3376:
3317:
3281:
3253:
3207:
3169:
3128:
3118:
3073:
3057:
3010:
2967:
2932:
2905:
2860:
2819:
2811:
2772:
2734:
2726:
2687:
2659:
2616:
2579:
2571:
2558:
Carballeira, N. M.; Reyes, M.; Sostre, A.; Huang, H.; Verhagen, M. F.; Adams, M. W. (2009).
2532:
2505:
2414:
2371:
2338:
2114:
1918:
1843:
1582:
1292:
920:
901:
28:
2101:
1238:
1655:
1537:
1394:
1305:
1267:
1057:
935:
818:
802:
778:
64:
2236:
the next in the series with an odd number. These compounds are weak dibasic acids with pK
1081:
dimethyl branching near the centre of the carbon chain have been discovered in the genus
2901:
2367:
2045:
1979:
3133:
3102:
3078:
3045:
2739:
2714:
2257:
2036:
1777:
1755:
1668:
1566:
1382:
1142:
1041:
991:
893:
877:
616:
262:
32:
3321:
3285:
3211:
2936:
2865:
2848:
2824:
2799:
2798:
Carballeira, NM; Reyes, M; Sostre, A; Huang, H; Verhagen, MF; Adams, MW (April 1997).
2584:
2559:
2509:
2446:. Biotechnology in Agriculture and Forestry. Springer Berlin Heidelberg. p. 231.
2273:
1808:
364:
3456:
3396:
3225:
3174:
3157:
2909:
2691:
2663:
2426:
2391:
2087:
1992:
1865:
1821:
1715:
1700:
1664:
1625:
1595:
1102:
1061:
1033:
1028:
1027:. Short and medium chain (up to 11 carbon atoms) dioic acids have been discovered in
987:
958:
Thapsic acid was isolated from the dried roots of the
Mediterranean "deadly carrot",
321:
287:
95:
91:
2815:
2784:
2636:
2575:
1527:
1492:
1464:
1436:
1400:
1375:
1351:
1327:
753:
694:
3030:
2987:
2023:
1941:
1588:
1559:
1410:
1273:
1251:
1244:
1187:
1177:
1161:
1083:
1048:. It was discovered that these compounds appeared in urine after administration of
897:
873:
861:
782:
726:
648:
522:
488:
423:
389:
253:
2536:
2342:
2205:
2183:
2051:
1963:
1902:
1896:
1792:
1369:
716:
667:
635:
603:
572:
562:
475:
444:
63:. In general, dicarboxylic acids show similar chemical behavior and reactivity to
2161:
2134:
2107:
1880:
1156:
2 (three other derivatives with different glycosylations are known) containing a
543:
509:
308:
2307:
2029:
2007:
1858:
1836:
1814:
1685:
1613:
1298:
1222:
1173:
1157:
1065:
927:
865:
842:
798:
786:
410:
376:
355:
342:
274:
240:
219:
99:
83:
3380:
1985:
1852:
1770:
1122:. The most abundant diacid was the C30 α,ω-13,16-dimethyloctacosanedioic acid.
3014:
2620:
1799:
1639:
1629:
1553:
1486:
1458:
1430:
1097:
1045:
931:
857:
774:
228:
3388:
3364:
3123:
2375:
2220:
1786:
1764:
1643:
1049:
972:
942:
885:
846:
822:
810:
806:
790:
625:
79:
75:
71:
56:
3329:
3293:
3219:
3183:
3142:
3022:
2944:
2628:
2544:
2383:
1830:
1679:
1607:
330:
296:
3087:
2979:
2874:
2833:
2699:
2593:
657:
531:
497:
432:
398:
2748:
2224:
1137:
1018:
965:
794:
166:
3232:(Subscription may be required or content may be available in libraries.)
2443:
Plant
Biotechnology for Sustainable Production of Energy and co-products
3257:
3069:
2971:
2776:
2418:
995:
159:
2730:
1719:
1714:
A series of alkyl- and alkenyl-itaconates, known as ceriporic acids (
1692:
1650:
1153:
912:
835:
829:
3061:
1129:
781:) with nitric acid. It is now produced industrially by oxidation of
1064:
is subjected to ω-oxidation and then tob-oxidation, this generates
1696:
1128:
1053:
1000:
976:
850:
87:
2713:
Klein, RA; Hazlewood, GP; Kemp, P; Dawson, RM (1 December 1979).
2652:
Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism
889:
3363:
Moghadas, Babak; Solouk, Atefeh; Sadeghi, Davoud (2020-08-24).
2267:
3156:
Bonaventure, Gustavo; Ohlrogge, John; Pollard, Mike (2004).
2244:
indicates they exist predominantly as dicarboxylate anions.
793:. It has several other industrial uses in the production of
82:. The most widely used dicarboxylic acid in the industry is
3103:"Bioactive constituents and medicinal importance of genus
3428:
Lipidomics gateway Structure Database Dicarboxylic acids
3101:
Sati, Sushil Chandra; Sati, Nitin; Sati, O. P. (2011).
2286:
106:; long chain aliphatic dicarboxylic acids are known as
2405:
Kadesch, Richard G. (November 1954). "Dibasic acids".
1646:
of occupational or environmental exposure to benzene.
3044:
Weaver VM, Davoli CT, Heller PJ, et al. (1996).
118:
The general formula for acyclic dicarboxylic acid is
2847:
Jung, S; Zeikus, JG; Hollingsworth, RI (June 1994).
955:. Traumatic acid is its monounsaturated counterpart.
2440:Mascia, P.N.; Scheffran, J.; Widholm, J.M. (2010).
872:, but now by oxidative cleavage of oleic acid with
2041:(2S,3S,4S,5R)-2,3,4,5-Tetrahydroxyhexanedioic acid
102:in the human body. The name can be abbreviated to
70:Dicarboxylic acids are used in the preparation of
90:. Other examples of dicarboxylic acids include
114:Linear and cyclic saturated dicarboxylic acids
2407:Journal of the American Oil Chemists' Society
8:
3352:. London: Oliver and Boyd. pp. 283–284.
1009:where their content can be higher than 50%.
86:, which is a precursor in the production of
3414:. London: Blackie & Son. p. 242.
3173:
3132:
3122:
3077:
2864:
2823:
2738:
2583:
1718:), were found in cultures of a selective
1077:Long-chain dicarboxylic acids containing
43:for dicarboxylic acids can be written as
2067:
1735:
1678:
1193:
773:. It was first obtained by oxidation of
173:
50:
46:
3343:
3341:
3339:
2330:
1040:Dicarboxylic acids may be produced by
16:Organic compound with two –COOH groups
3435:"Trivial names of fatty acids-Part 1"
7:
3200:Bioorganic & Medicinal Chemistry
2472:
2470:
2019:(2R,6S)-2,6-Diaminoheptanedioic acid
926:Brassylic acid can be produced from
14:
3322:10.1016/j.chemphyslip.2009.03.006
1936:2,3,4-Trihydroxypentanedioic acid
1073:Branched-chain dicarboxylic acids
3175:10.1111/j.1365-313X.2004.02258.x
2910:10.1016/j.orggeochem.2007.08.013
2272:
2225:PET, Terylene, Dacron and Lavsan
2198:
2195:2,6-Naphthalenedicarboxylic acid
2191:2,6-Naphthalenedicarboxylic acid
2176:
2154:
2127:
2100:
2044:
2022:
2000:
1978:
1956:
1917:
1895:
1873:
1851:
1829:
1807:
1785:
1763:
1667:, is present in Arabidopsis and
1606:
1581:
1552:
1485:
1457:
1429:
1393:
1368:
1344:
1320:
1291:
1266:
1237:
911:Sebacic acid, named from sebum (
900:properties against a variety of
880:resins, rubber), lubricants and
715:
656:
624:
592:
561:
530:
496:
464:
460:1,4-Cyclohexanedicarboxylic acid
431:
397:
363:
329:
295:
261:
227:
3310:Chemistry and Physics of Lipids
3274:Chemistry and Physics of Lipids
2816:10.1128/jb.179.8.2766-2768.1997
2576:10.1128/jb.179.8.2766-2768.1997
2219:used in the manufacture of the
2173:2-(2-Carboxyphenyl)benzoic acid
2170:Biphenyl-2,2′-dicarboxylic acid
789:, mainly for the production of
2242:Henderson–Hasselbalch equation
1730:Substituted dicarboxylic acids
1501:(Allene-1,3-dicarboxylic acid)
1168:Unsaturated dicarboxylic acids
1146:) and the fruits of gardenia (
1119:Thermoanaerobacter ethanolicus
934:, but also by microorganisms (
884:. Azelaic acid is now used in
1:
3286:10.1016/S0009-3084(03)00098-7
3212:10.1016/S0968-0896(99)00312-0
2937:10.1016/S0021-9673(99)00600-7
2866:10.1016/S0022-2275(20)40101-4
2537:10.1016/j.tplants.2008.03.003
2510:10.1016/S0308-8146(01)00308-9
2343:10.1002/14356007.a08_523.pub3
2223:known by brand names such as
2151:Benzene-1,4-dicarboxylic acid
2124:Benzene-1,3-dicarboxylic acid
2097:Benzene-1,2-dicarboxylic acid
1826:2,3-Dihydroxybutanedioic acid
1649:Glutinic acid, a substituted
1600:2-Methylidenebutanedioic acid
1575:)-2-Methyl-2-butenedioic acid
1546:)-2-Methylbut-2-enedioic acid
2692:10.1016/0003-2697(87)90155-2
2664:10.1016/0005-2760(77)90002-9
1044:of fatty acids during their
830:
2925:Journal of Chromatography A
2062:Aromatic dicarboxylic acids
1628:after conversion into oxo-
3479:
3381:10.1007/s00289-020-03352-8
1914:2-hydroxypentanedioic acid
1760:2-Hydroxypropanedioic acid
1479:)-Hexa-2,4-dienedioic acid
1451:)-Hexa-2,4-dienedioic acid
1423:)-Hexa-2,4-dienedioic acid
1281:Acetylenedicarboxylic acid
1181:
1171:
990:, likely in relation with
821:, urethane and also as an
3015:10.1080/01926230601156278
2853:Journal of Lipid Research
1533:
1510:Penta-2,3-dienedioic acid
1409:
1406:
1304:
1218:
906:anaerobic micro-organisms
3348:Schmidt, Julius (1955).
3050:Environ. Health Perspect
2765:Archives of Microbiology
1997:2-Aminopentanedioic acid
1949:Acetonedicarboxylic acid
845:and in the synthesis of
3124:10.4103/0973-7847.91115
2960:Plant Molecular Biology
2804:Journal of Bacteriology
2719:The Biochemical Journal
2680:Analytical Biochemistry
2621:10.1023/A:1002837830653
2525:Trends in Plant Science
2376:10.1126/science.1170025
2362:(3 April 2009): 89–91.
2215:Terephthalic acid is a
1870:2-Aminobutanedioic acid
1804:Hydroxybutanedioic acid
801:, gelatinizing agents,
3410:Bernthsen, A. (1922).
1975:2-Oxopentanedioic acid
1953:3-Oxopentanedioic acid
1910:α-hydroxyGlutaric acid
1688:
1338:)-Pent-2-enedioic acid
1314:)-Pent-2-enedioic acid
1134:
870:potassium permanganate
3439:lipidlibrary.aocs.org
3111:Pharmacognosy Reviews
3003:Toxicologic Pathology
2609:Biochemistry (Moscow)
1892:dioxobutanedioic acid
1682:
1387:Dodec-2-enedioic acid
1132:
1105:, bacteria living in
744:triacontanedioic acid
685:heneicosanedioic acid
188:Systematic IUPAC name
3433:Dijkstra, Albert J.
2890:Organic Geochemistry
1782:Oxopropanedioic acid
1711:inhibitory effects.
1653:, was isolated from
1149:Gardenia jasminoides
1006:Arabidopsis thaliana
828:Pimelic acid (Greek
653:hexadecanedioic acid
65:monocarboxylic acids
2902:2008OrGeo..39..152B
2368:2009Sci...324...89W
2069:
2015:Diaminopimelic acid
1971:α-Ketoglutaric acid
1848:Oxobutanedioic acid
1737:
1722:-degrading fungus (
1709:farnesyltransferase
1638:-Muconic acid is a
1285:But-2-ynedioic acid
1195:
1184:Cis–trans isomerism
1111:Thermotoga maritima
1024:Pyrococcus furiosus
917:diffusion pump oils
771:oxidative rancidity
621:tridecanedioic acid
175:
3463:Dicarboxylic acids
3258:10.1246/cl.2000.54
2972:10.1007/BF00016483
2777:10.1007/BF00409880
2419:10.1007/BF02638574
2320:Tricarboxylic acid
2254:succinic anhydride
2217:commodity chemical
2068:
1888:dioxosuccinic acid
1747:Structural formula
1736:
1689:
1361:2-Decenedioic acid
1260:)-Butenedioic acid
1231:)-Butenedioic acid
1211:Structural formula
1194:
1135:
1012:It was shown that
952:Candida tropicalis
815:polyurethane foams
711:docosanedioic acid
588:dodecanedioic acid
558:undecanedioic acid
174:
3412:Organic Chemistry
3350:Organic Chemistry
3246:Chemistry Letters
3224: – via
3162:The Plant Journal
2731:10.1042/bj1830691
2453:978-3-642-13440-1
2303:
2302:
2211:
2210:
2142:Terephthalic acid
2057:
2056:
1716:Pub Chem 52921868
1619:
1618:
1107:solfatara springs
1014:hyperthermophilic
961:Thapsia garganica
890:treatment of acne
759:
758:
394:heptanedioic acid
326:pentanedioic acid
258:propanedioic acid
55:, where R can be
41:molecular formula
25:dicarboxylic acid
21:organic chemistry
3470:
3449:
3447:
3445:
3416:
3415:
3407:
3401:
3400:
3375:(9): 4919–4929.
3369:Polymer Bulletin
3360:
3354:
3353:
3345:
3334:
3333:
3304:
3298:
3297:
3268:
3262:
3261:
3240:
3234:
3233:
3230:
3223:
3194:
3188:
3187:
3177:
3153:
3147:
3146:
3136:
3126:
3098:
3092:
3091:
3081:
3041:
3035:
3034:
2998:
2992:
2991:
2966:(5): 1423–1437.
2955:
2949:
2948:
2920:
2914:
2913:
2885:
2879:
2878:
2868:
2844:
2838:
2837:
2827:
2795:
2789:
2788:
2759:
2753:
2752:
2742:
2710:
2704:
2703:
2674:
2668:
2667:
2647:
2641:
2640:
2604:
2598:
2597:
2587:
2570:(8): 2766–2768.
2555:
2549:
2548:
2520:
2514:
2513:
2493:
2487:
2486:
2474:
2465:
2464:
2462:
2460:
2437:
2431:
2430:
2402:
2396:
2395:
2351:
2345:
2335:
2298:
2295:
2276:
2268:
2202:
2180:
2158:
2131:
2115:Isophthalic acid
2104:
2070:
2048:
2026:
2004:
1982:
1960:
1921:
1899:
1877:
1855:
1844:Oxaloacetic acid
1833:
1811:
1789:
1767:
1738:
1724:white rot fungus
1610:
1585:
1556:
1489:
1461:
1433:
1397:
1372:
1348:
1324:
1295:
1270:
1241:
1196:
921:synthetic rubber
833:
803:hydraulic fluids
740:Equisetolic acid
719:
707:Phellogenic acid
660:
628:
596:
565:
534:
527:decanedioic acid
500:
493:nonanedioic acid
468:
435:
428:octanedioic acid
401:
367:
360:hexanedioic acid
333:
299:
292:butanedioic acid
265:
231:
224:ethanedioic acid
176:
157:
155:
154:
146:
145:
137:
136:
128:
127:
54:
38:
29:organic compound
3478:
3477:
3473:
3472:
3471:
3469:
3468:
3467:
3453:
3452:
3443:
3441:
3432:
3424:
3419:
3409:
3408:
3404:
3362:
3361:
3357:
3347:
3346:
3337:
3306:
3305:
3301:
3270:
3269:
3265:
3242:
3241:
3237:
3231:
3228:
3196:
3195:
3191:
3155:
3154:
3150:
3117:(10): 174–183.
3100:
3099:
3095:
3062:10.2307/3432891
3043:
3042:
3038:
3000:
2999:
2995:
2957:
2956:
2952:
2922:
2921:
2917:
2887:
2886:
2882:
2846:
2845:
2841:
2797:
2796:
2792:
2761:
2760:
2756:
2712:
2711:
2707:
2676:
2675:
2671:
2649:
2648:
2644:
2606:
2605:
2601:
2557:
2556:
2552:
2522:
2521:
2517:
2495:
2494:
2490:
2476:
2475:
2468:
2458:
2456:
2454:
2439:
2438:
2434:
2413:(11): 568–573.
2404:
2403:
2399:
2353:
2352:
2348:
2336:
2332:
2328:
2316:
2299:
2293:
2290:
2283:needs expansion
2277:
2266:
2239:
2233:
2169:
2144:
2117:
2090:
2064:
1932:Arabinaric acid
1732:
1684:
1677:
1675:Alkylitaconates
1656:Alnus glutinosa
1538:Citraconic acid
1523:
1519:
1500:
1306:Glutaconic acid
1219:Monounsaturated
1190:
1180:
1172:Main articles:
1170:
1075:
1058:cytochrome P450
892:). It displays
819:leather tanning
779:ricinoleic acid
766:
204:
197:
153:
150:
149:
148:
144:
141:
140:
139:
135:
132:
131:
130:
126:
123:
122:
121:
119:
116:
52:
48:
44:
39:). The general
36:
33:carboxyl groups
31:containing two
17:
12:
11:
5:
3476:
3474:
3466:
3465:
3455:
3454:
3451:
3450:
3430:
3423:
3422:External links
3420:
3418:
3417:
3402:
3355:
3335:
3299:
3280:(2): 121–131.
3263:
3235:
3189:
3168:(6): 920–930.
3148:
3093:
3036:
2993:
2950:
2931:(2): 349–355.
2915:
2896:(1): 152–156.
2880:
2859:(6): 1057–65.
2839:
2790:
2771:(4): 324–333.
2754:
2725:(3): 691–700.
2705:
2686:(2): 213–221.
2669:
2658:(2): 261–268.
2642:
2599:
2550:
2515:
2504:(4): 469–473.
2498:Food Chemistry
2488:
2466:
2452:
2432:
2397:
2346:
2329:
2327:
2324:
2323:
2322:
2315:
2312:
2301:
2300:
2294:September 2024
2280:
2278:
2271:
2265:
2262:
2258:cyclopentanone
2237:
2232:
2229:
2213:
2212:
2209:
2208:
2203:
2196:
2193:
2187:
2186:
2181:
2174:
2171:
2165:
2164:
2159:
2152:
2149:
2148:-phthalic acid
2138:
2137:
2132:
2125:
2122:
2121:-phthalic acid
2111:
2110:
2105:
2098:
2095:
2094:-phthalic acid
2084:
2083:
2080:
2077:
2074:
2063:
2060:
2059:
2058:
2055:
2054:
2049:
2042:
2039:
2037:Saccharic acid
2033:
2032:
2027:
2020:
2017:
2011:
2010:
2005:
1998:
1995:
1989:
1988:
1983:
1976:
1973:
1967:
1966:
1961:
1954:
1951:
1945:
1944:
1939:
1937:
1934:
1928:
1927:
1922:
1915:
1912:
1906:
1905:
1900:
1893:
1890:
1884:
1883:
1878:
1871:
1868:
1862:
1861:
1856:
1849:
1846:
1840:
1839:
1834:
1827:
1824:
1818:
1817:
1812:
1805:
1802:
1796:
1795:
1790:
1783:
1780:
1778:Mesoxalic acid
1774:
1773:
1768:
1761:
1758:
1756:Tartronic acid
1752:
1751:
1748:
1745:
1742:
1731:
1728:
1676:
1673:
1669:Brassica napus
1659:(Betulaceae).
1626:hydroperoxides
1621:
1620:
1617:
1616:
1611:
1604:
1601:
1598:
1592:
1591:
1586:
1579:
1576:
1569:
1567:Mesaconic acid
1563:
1562:
1557:
1550:
1547:
1540:
1535:
1531:
1530:
1525:
1521:
1517:
1514:
1512:
1502:
1496:
1495:
1490:
1483:
1480:
1468:
1467:
1462:
1455:
1452:
1440:
1439:
1434:
1427:
1424:
1413:
1408:
1404:
1403:
1398:
1391:
1388:
1385:
1383:Traumatic acid
1379:
1378:
1373:
1366:
1363:
1358:
1355:
1354:
1349:
1342:
1339:
1331:
1330:
1325:
1318:
1315:
1308:
1302:
1301:
1296:
1289:
1288:not applicable
1286:
1283:
1277:
1276:
1271:
1264:
1261:
1254:
1248:
1247:
1242:
1235:
1232:
1225:
1220:
1216:
1215:
1212:
1209:
1206:
1203:
1200:
1169:
1166:
1143:Crocus sativus
1089:diabolic acids
1074:
1071:
992:photosynthesis
970:
969:
956:
946:
924:
909:
894:bacteriostatic
878:vinyl chloride
854:
839:
826:
765:
762:
761:
760:
757:
756:
751:
749:
747:
745:
742:
737:
734:
730:
729:
724:
722:
720:
713:
708:
705:
702:
698:
697:
692:
690:
688:
686:
683:
678:
675:
671:
670:
665:
663:
661:
654:
651:
646:
643:
639:
638:
633:
631:
629:
622:
619:
617:Brassylic acid
614:
611:
607:
606:
601:
599:
597:
590:
585:
583:
580:
576:
575:
570:
568:
566:
559:
556:
554:
551:
547:
546:
541:
538:
535:
528:
525:
520:
517:
513:
512:
507:
504:
501:
494:
491:
486:
483:
479:
478:
473:
471:
469:
462:
457:
455:
452:
448:
447:
442:
439:
436:
429:
426:
421:
418:
414:
413:
408:
405:
402:
395:
392:
387:
384:
380:
379:
374:
371:
368:
361:
358:
353:
350:
346:
345:
340:
337:
334:
327:
324:
319:
316:
312:
311:
306:
303:
300:
293:
290:
285:
282:
278:
277:
272:
269:
266:
259:
256:
251:
248:
244:
243:
238:
235:
232:
225:
222:
217:
214:
210:
209:
206:
202:
199:
195:
192:
189:
186:
183:
180:
151:
142:
133:
124:
115:
112:
15:
13:
10:
9:
6:
4:
3:
2:
3475:
3464:
3461:
3460:
3458:
3440:
3436:
3431:
3429:
3426:
3425:
3421:
3413:
3406:
3403:
3398:
3394:
3390:
3386:
3382:
3378:
3374:
3370:
3366:
3359:
3356:
3351:
3344:
3342:
3340:
3336:
3331:
3327:
3323:
3319:
3315:
3311:
3303:
3300:
3295:
3291:
3287:
3283:
3279:
3275:
3267:
3264:
3259:
3255:
3251:
3247:
3239:
3236:
3227:
3226:ScienceDirect
3221:
3217:
3213:
3209:
3206:(3): 571–80.
3205:
3201:
3193:
3190:
3185:
3181:
3176:
3171:
3167:
3163:
3159:
3152:
3149:
3144:
3140:
3135:
3130:
3125:
3120:
3116:
3112:
3108:
3106:
3097:
3094:
3089:
3085:
3080:
3075:
3071:
3067:
3063:
3059:
3056:(3): 318–23.
3055:
3051:
3047:
3040:
3037:
3032:
3028:
3024:
3020:
3016:
3012:
3008:
3004:
2997:
2994:
2989:
2985:
2981:
2977:
2973:
2969:
2965:
2961:
2954:
2951:
2946:
2942:
2938:
2934:
2930:
2926:
2919:
2916:
2911:
2907:
2903:
2899:
2895:
2891:
2884:
2881:
2876:
2872:
2867:
2862:
2858:
2854:
2850:
2843:
2840:
2835:
2831:
2826:
2821:
2817:
2813:
2810:(8): 2766–8.
2809:
2805:
2801:
2794:
2791:
2786:
2782:
2778:
2774:
2770:
2766:
2758:
2755:
2750:
2746:
2741:
2736:
2732:
2728:
2724:
2720:
2716:
2709:
2706:
2701:
2697:
2693:
2689:
2685:
2681:
2673:
2670:
2665:
2661:
2657:
2653:
2646:
2643:
2638:
2634:
2630:
2626:
2622:
2618:
2614:
2610:
2603:
2600:
2595:
2591:
2586:
2581:
2577:
2573:
2569:
2565:
2561:
2554:
2551:
2546:
2542:
2538:
2534:
2530:
2526:
2519:
2516:
2511:
2507:
2503:
2499:
2492:
2489:
2484:
2480:
2473:
2471:
2467:
2455:
2449:
2445:
2444:
2436:
2433:
2428:
2424:
2420:
2416:
2412:
2408:
2401:
2398:
2393:
2389:
2385:
2381:
2377:
2373:
2369:
2365:
2361:
2357:
2350:
2347:
2344:
2340:
2334:
2331:
2325:
2321:
2318:
2317:
2313:
2311:
2309:
2297:
2288:
2284:
2281:This section
2279:
2275:
2270:
2269:
2263:
2261:
2259:
2255:
2249:
2245:
2243:
2230:
2228:
2226:
2222:
2218:
2207:
2204:
2201:
2197:
2194:
2192:
2189:
2188:
2185:
2182:
2179:
2175:
2172:
2168:Diphenic acid
2167:
2166:
2163:
2160:
2157:
2153:
2150:
2147:
2143:
2140:
2139:
2136:
2133:
2130:
2126:
2123:
2120:
2116:
2113:
2112:
2109:
2106:
2103:
2099:
2096:
2093:
2089:
2088:Phthalic acid
2086:
2085:
2081:
2078:
2075:
2072:
2071:
2066:
2065:
2061:
2053:
2050:
2047:
2043:
2040:
2038:
2035:
2034:
2031:
2028:
2025:
2021:
2018:
2016:
2013:
2012:
2009:
2006:
2003:
1999:
1996:
1994:
1993:Glutamic acid
1991:
1990:
1987:
1984:
1981:
1977:
1974:
1972:
1969:
1968:
1965:
1962:
1959:
1955:
1952:
1950:
1947:
1946:
1943:
1940:
1938:
1935:
1933:
1930:
1929:
1926:
1923:
1920:
1916:
1913:
1911:
1908:
1907:
1904:
1901:
1898:
1894:
1891:
1889:
1886:
1885:
1882:
1879:
1876:
1872:
1869:
1867:
1866:Aspartic acid
1864:
1863:
1860:
1857:
1854:
1850:
1847:
1845:
1842:
1841:
1838:
1835:
1832:
1828:
1825:
1823:
1822:Tartaric acid
1820:
1819:
1816:
1813:
1810:
1806:
1803:
1801:
1798:
1797:
1794:
1791:
1788:
1784:
1781:
1779:
1776:
1775:
1772:
1769:
1766:
1762:
1759:
1757:
1754:
1753:
1749:
1746:
1743:
1740:
1739:
1734:
1733:
1729:
1727:
1725:
1721:
1717:
1712:
1710:
1706:
1702:
1701:itaconic acid
1698:
1694:
1687:
1683:Itaconic acid
1681:
1674:
1672:
1670:
1666:
1665:linoleic acid
1660:
1658:
1657:
1652:
1647:
1645:
1641:
1637:
1633:
1631:
1627:
1615:
1612:
1609:
1605:
1602:
1599:
1597:
1596:Itaconic acid
1594:
1593:
1590:
1587:
1584:
1580:
1577:
1574:
1570:
1568:
1565:
1564:
1561:
1558:
1555:
1551:
1548:
1545:
1541:
1539:
1536:
1532:
1529:
1526:
1515:
1513:
1511:
1507:
1503:
1499:Glutinic acid
1498:
1497:
1494:
1491:
1488:
1484:
1481:
1478:
1474:
1470:
1469:
1466:
1463:
1460:
1456:
1453:
1450:
1446:
1442:
1441:
1438:
1435:
1432:
1428:
1425:
1422:
1418:
1414:
1412:
1407:Diunsaturated
1405:
1402:
1399:
1396:
1392:
1389:
1386:
1384:
1381:
1380:
1377:
1374:
1371:
1367:
1364:
1362:
1359:
1357:
1356:
1353:
1350:
1347:
1343:
1340:
1337:
1333:
1332:
1329:
1326:
1323:
1319:
1316:
1313:
1309:
1307:
1303:
1300:
1297:
1294:
1290:
1287:
1284:
1282:
1279:
1278:
1275:
1272:
1269:
1265:
1262:
1259:
1255:
1253:
1250:
1249:
1246:
1243:
1240:
1236:
1233:
1230:
1226:
1224:
1221:
1217:
1213:
1210:
1207:
1204:
1201:
1198:
1197:
1192:
1191:
1189:
1185:
1179:
1175:
1167:
1165:
1163:
1159:
1155:
1151:
1150:
1145:
1144:
1139:
1131:
1127:
1123:
1121:
1120:
1114:
1112:
1108:
1104:
1103:Thermotogales
1101:of the order
1100:
1099:
1094:
1090:
1086:
1085:
1080:
1072:
1070:
1067:
1063:
1062:palmitic acid
1059:
1055:
1051:
1047:
1043:
1038:
1036:
1035:
1034:Aphanizomenon
1031:of the genus
1030:
1029:Cyanobacteria
1026:
1025:
1020:
1015:
1010:
1008:
1007:
1002:
997:
993:
989:
988:succinic acid
984:
982:
978:
974:
967:
963:
962:
957:
954:
953:
947:
944:
940:
938:
933:
929:
925:
922:
918:
914:
910:
907:
903:
899:
895:
891:
887:
883:
879:
875:
871:
867:
863:
859:
855:
852:
848:
844:
840:
837:
832:
827:
824:
820:
816:
812:
808:
804:
800:
796:
792:
788:
784:
780:
776:
772:
768:
767:
763:
755:
752:
750:
748:
746:
743:
741:
738:
735:
732:
731:
728:
725:
723:
721:
718:
714:
712:
709:
706:
703:
700:
699:
696:
693:
691:
689:
687:
684:
682:
679:
676:
673:
672:
669:
666:
664:
662:
659:
655:
652:
650:
647:
644:
641:
640:
637:
634:
632:
630:
627:
623:
620:
618:
615:
612:
609:
608:
605:
602:
600:
598:
595:
591:
589:
586:
584:
581:
578:
577:
574:
571:
569:
567:
564:
560:
557:
555:
552:
549:
548:
545:
542:
539:
536:
533:
529:
526:
524:
521:
518:
515:
514:
511:
508:
505:
502:
499:
495:
492:
490:
487:
484:
481:
480:
477:
474:
472:
470:
467:
463:
461:
458:
456:
453:
450:
449:
446:
443:
440:
437:
434:
430:
427:
425:
422:
419:
416:
415:
412:
409:
406:
403:
400:
396:
393:
391:
388:
385:
382:
381:
378:
375:
372:
369:
366:
362:
359:
357:
354:
351:
348:
347:
344:
341:
338:
335:
332:
328:
325:
323:
322:Glutaric acid
320:
317:
314:
313:
310:
307:
304:
301:
298:
294:
291:
289:
288:Succinic acid
286:
283:
280:
279:
276:
273:
270:
267:
264:
260:
257:
255:
252:
249:
246:
245:
242:
239:
236:
233:
230:
226:
223:
221:
218:
215:
212:
211:
207:
200:
193:
190:
187:
184:
181:
178:
177:
172:
171:
170:
168:
163:
161:
113:
111:
109:
108:fatty diacids
105:
101:
97:
96:glutamic acid
93:
92:aspartic acid
89:
85:
81:
77:
73:
68:
66:
62:
58:
42:
34:
30:
26:
22:
3442:. Retrieved
3438:
3411:
3405:
3372:
3368:
3358:
3349:
3316:(2): 77–80.
3313:
3309:
3302:
3277:
3273:
3266:
3252:(1): 54–55.
3249:
3245:
3238:
3203:
3199:
3192:
3165:
3161:
3151:
3114:
3110:
3104:
3096:
3053:
3049:
3039:
3009:(2): 268–9.
3006:
3002:
2996:
2963:
2959:
2953:
2928:
2924:
2918:
2893:
2889:
2883:
2856:
2852:
2842:
2807:
2803:
2793:
2768:
2764:
2757:
2722:
2718:
2708:
2683:
2679:
2672:
2655:
2651:
2645:
2615:(1): 72–76.
2612:
2608:
2602:
2567:
2564:J. Bacteriol
2563:
2553:
2531:(5): 89–91.
2528:
2524:
2518:
2501:
2497:
2491:
2482:
2478:
2457:. Retrieved
2442:
2435:
2410:
2406:
2400:
2359:
2355:
2349:
2333:
2304:
2291:
2287:adding to it
2282:
2250:
2246:
2234:
2214:
2145:
2118:
2091:
2073:Common names
1713:
1690:
1661:
1654:
1648:
1635:
1634:
1622:
1572:
1543:
1505:
1476:
1472:
1448:
1444:
1426:trans,trans
1420:
1416:
1411:Muconic acid
1335:
1311:
1257:
1252:Fumaric acid
1228:
1188:E-Z notation
1178:Fumaric acid
1162:disaccharide
1147:
1141:
1136:
1124:
1117:
1115:
1096:
1093:Butyrivibrio
1092:
1088:
1084:Butyrivibrio
1082:
1076:
1039:
1032:
1022:
1011:
1004:
1003:, except in
985:
980:
971:
959:
950:
936:
898:bactericidal
874:chromic acid
862:elaidic acid
843:alkyd resins
799:plasticizers
783:cyclohexanol
681:Japanic acid
649:Thapsic acid
523:Sebacic acid
489:Azelaic acid
424:Suberic acid
390:Pimelic acid
254:Malonic acid
164:
117:
107:
103:
69:
24:
18:
2308:succinimide
2264:Derivatives
1741:Common name
1705:Chaetomella
1686:PubChem 811
1636:trans,trans
1630:fatty acids
1223:Maleic acid
1202:Common name
1174:Maleic acid
1158:gentiobiose
1066:malonyl-CoA
1042:ω-oxidation
928:erucic acid
866:linseed oil
787:cyclohexane
356:Adipic acid
220:Oxalic acid
185:Common name
100:amino acids
84:adipic acid
2485:: 568–571.
2326:References
2231:Properties
2076:IUPAC name
1800:Malic acid
1744:IUPAC name
1640:metabolite
1520:CCH=C=CHCO
1205:IUPAC name
1182:See also:
1098:Thermotoga
1046:catabolism
932:ozonolysis
858:oleic acid
853:variants).
847:polyamides
811:emollients
807:lubricants
775:castor oil
764:Occurrence
80:polyesters
76:polyamides
72:copolymers
3397:221283821
3389:1436-2449
2427:189786702
2392:206518245
2221:polyester
2079:Structure
1671:cuticle.
1644:biomarker
1454:cis,trans
1050:tricaprin
973:Japan wax
943:tridecane
886:cosmetics
825:in foods.
823:acidulant
795:adhesives
791:Nylon 6-6
191:Structure
57:aliphatic
3457:Category
3330:19477313
3294:14623447
3220:10732974
3184:15584957
3143:22279375
3023:17366320
2945:10457433
2785:12709437
2637:34894138
2629:11240396
2545:18440267
2384:19342588
2314:See also
2082:PubChem
1750:PubChem
1534:Branched
1214:PubChem
1138:Crocetin
1133:Crocetin
1019:archaeon
966:Apiaceae
208:PubChem
167:mnemonic
74:such as
61:aromatic
3444:24 June
3134:3263052
3088:8919771
3079:1469300
3070:3432891
3031:6392962
2988:3712976
2980:7858198
2898:Bibcode
2875:8077844
2834:9098079
2740:1161651
2700:2831753
2594:9098079
2364:Bibcode
2356:Science
1693:lichens
1528:5242834
1493:5280518
1482:cis,cis
1437:5356793
1401:5283028
1376:6442613
1352:5280498
1328:5370328
1079:vicinal
996:suberin
941:) from
937:Candida
902:aerobic
882:greases
754:5322010
695:9543668
160:PubChem
3395:
3387:
3328:
3292:
3229:
3218:
3182:
3141:
3131:
3086:
3076:
3068:
3029:
3021:
2986:
2978:
2943:
2873:
2832:
2825:179030
2822:
2783:
2749:540040
2747:
2737:
2698:
2635:
2627:
2592:
2585:179030
2582:
2543:
2479:Inform
2459:18 May
2450:
2425:
2390:
2382:
1942:109475
1720:lignin
1651:allene
1589:638129
1560:643798
1465:280518
1274:444972
1245:444266
1208:Isomer
1154:crocin
983:sp.).
979:tree (
913:tallow
836:lysine
831:pimelh
727:244872
158:. The
104:diacid
98:, two
49:C−R−CO
27:is an
3393:S2CID
3105:Alnus
3066:JSTOR
3027:S2CID
2984:S2CID
2781:S2CID
2633:S2CID
2423:S2CID
2388:S2CID
2206:14357
2184:10210
2052:33037
1964:68328
1903:82062
1793:10132
1697:fungi
1578:trans
1390:trans
1365:trans
1341:trans
1263:trans
1054:NADPH
1001:cutin
977:sumac
851:nylon
668:10459
636:10458
604:12736
573:15816
540:5.450
537:4.720
506:5.498
503:4.550
476:14106
445:10457
441:5.498
438:4.526
88:nylon
37:−COOH
3446:2019
3385:ISSN
3326:PMID
3290:PMID
3216:PMID
3180:PMID
3139:PMID
3084:PMID
3019:PMID
2976:PMID
2941:PMID
2871:PMID
2830:PMID
2745:PMID
2696:PMID
2625:PMID
2590:PMID
2541:PMID
2461:2021
2448:ISBN
2380:PMID
2162:7489
2135:8496
2108:1017
1881:5960
1695:and
1199:Type
1186:and
1176:and
1056:and
981:Rhus
904:and
896:and
733:C30
701:C22
674:C21
642:C16
610:C13
579:C12
550:C11
544:5192
516:C10
510:2266
407:5.43
404:4.50
373:5.41
370:4.41
339:5.41
336:4.34
309:1110
305:5.41
302:4.21
271:5.05
268:2.85
237:4.27
234:1.27
129:C(CH
94:and
78:and
23:, a
3377:doi
3318:doi
3314:159
3282:doi
3278:126
3254:doi
3208:doi
3170:doi
3129:PMC
3119:doi
3074:PMC
3058:doi
3054:104
3011:doi
2968:doi
2933:doi
2929:849
2906:doi
2861:doi
2820:PMC
2812:doi
2808:179
2773:doi
2769:144
2735:PMC
2727:doi
2723:183
2688:doi
2684:167
2660:doi
2656:487
2617:doi
2580:PMC
2572:doi
2568:179
2533:doi
2506:doi
2415:doi
2372:doi
2360:324
2339:doi
2289:.
2030:865
2008:611
1859:970
1837:875
1815:525
1614:811
1549:cis
1317:cis
1299:371
1234:cis
939:sp.
930:by
860:or
785:or
482:C9
451:C8
417:C8
411:385
383:C7
377:196
349:C6
343:743
315:C5
281:C4
275:867
247:C3
241:971
213:C2
59:or
19:In
3459::
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3383:.
3373:78
3371:.
3367:.
3338:^
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2469:^
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2411:31
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2310:.
2260:.
2227:.
1986:51
1925:43
1771:45
1699:,
1632:.
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1508:)-
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1475:,4
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817:,
813:,
809:,
805:,
797:,
736:28
704:20
677:19
645:14
613:11
582:10
201:pK
194:pK
179:C
147:CO
120:HO
110:.
67:.
45:HO
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Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
