24:
179:
508:
of this compound, that differ in the orientation of the four hydroxyls relative to the mean plane of the ring. They can be denoted by the letter "α" or "β" after each carbon index ("2α","2β","4β", etc.), to indicate the corresponding side of the plane relative to the 1-hydroxyl; or by listing all
579:
Methods which have been employed for the preparation of 1,2,4,5-cyclohexanetetrols include: reduction or hydrogenation of (1) tri-hydroxycyclohexanones, (2) hydroxylated aromatics, or (3) hydroxylated quinones; the (4) hydrogenolysis of dibromocyclohexanetetrols; the (5) hydration of
917:
T. Posternak and D. Reymond (1955): "Recherches dans la série des cyclitols XXI. Sur la configuration de cyclohexane-tétrols et -triols optiquement actifs. Sur l'oxydation biochimique du cyclohexane-tétrol-1,4/2,3 (dihydro-conduritol)".
728:
Ahmet Maras, Mesut Erden, Hasan Seçen, and Yasar Sütbeyaz (1998): "One-pot synthesis from 1,4-cyclohexadiene of (±)-1,4/2,5-cyclohexanetetrol, a naturally occurring cyclitol derivative".
897:
Théodore
Posternak and Dominique Reymond (1953): "Recherches dans la série des cyclitols XVII. Sur l'oxydation de divers cyclitols par Acetobacter suboxydans".
218:
833:
Nihat
Akbulut and Metin Balci (1988): "A new and stereospecific synthesis of cyclitols: (1,2,4/3)-, (1,2/3,4)-, and (1,3/2,4)-cyclohexanetetrols".
193:
877:
Th. Posternak and H. Friedli (1953): "Recherches dans la série des cyclitols XVI. Sur quelques cyclohexane-tétrols-1,2,3,4".
157:
347:
706:
Synthesis of the Five
Diastereomeric 1,2,4,5-Cyclohexanetetrols. Nuclear Magnetic Resonance Configurational Proofs
100:
853:
J. S. Craigie (1969): "Some
Salinity-Induced Changes in Growth, Pigments, and Cyclohexanetetrol Content of
949:
681:
CON and CBN IUPAC Commissions on
Nomenclature (1968): "The Nomenclature of Cyclitols - Tentative Rules".
23:
643:. The yield was 88%, with no trace of the 1,5/2,4 isomer. The racemic 1,4/2,5 isomer is soluble in
174:
40:
66:
599:
584:
477:
787:
G. Mehta, S. Sen and S. Dey (2005). "(1S*,2S*,4S*,5S*)-Cyclohexane-1,2,4,5-tetrol monohydrate".
607:
509:
the "α" indices, then a slash "/", then the "β" indices (or "0" if the second list is empty).
481:
648:
944:
923:
902:
882:
862:
838:
792:
733:
713:
686:
636:
402:
390:
378:
313:
241:
120:
647:, and yields colorless crystals with melting point 194–196 °C. The (+) enantiomer is
580:
diepoxycyclohexanes; and the hydroxylation of (6) cyclohexadienes or (7) cyclohexenediols.
76:
178:
690:
341:
737:
938:
603:
302:
292:
587:
and others reported the synthesis of racemic 1,4/2,5-cyclohexanetetrol (the chiral
145:
761:
J.D. Ramanathan, J.S. Craigie, J. McLachlan, D.G. Smith, and A.G. McInnes (1966):
382:
329:
796:
656:
652:
269:
111:
927:
906:
886:
640:
632:
704:
G. E. McCasland, Stanley Furuta, L. F. Johnson, and J. N. Shoolery (1963):
660:
493:
394:
386:
842:
717:
644:
282:
132:
655:. The pure 1α,2α,4α,5α enantiomer crystallize as a monohydrate in the
505:
496:. Some of them have biologically important roles in some organisms.
489:
485:
473:
398:
866:
340:
Except where otherwise noted, data are given for materials in their
99:
89:
162:
774:
J. S. Craigie, J. McLachlan, and R. D. Tocher (1968):
297:
91.3 °C (196.3 °F; 364.4 K) estimated
202:
InChI=1S/C6H12O4/c7-3-1-4(8)6(10)2-5(3)9/h3-10H,1-2H2
859:Journal of the Fisheries Research Board of Canada
732:, volume 308, issues 3–4, April , Pages 435-437.
530:, with all hydroxyls on the same side (achiral).
144:
75:
29:Generic structure of 1,2,4,5-cyclohexanetetrol
8:
663:, b = 7.3502 Å, c = 5.1968 Å, β = 103.877°)
397:atoms on two non-adjacent pairs of adjacent
700:
698:
677:
675:
177:
119:
15:
861:, volume 26, issue 11, pages 2959-2967.
837:, volume 53, issue 14, pages 3338-3342.
651:, a natural product first identified in
671:
223:
198:
173:
922:, volume 38, issue 1, pages 195-205.
901:, volume 36, issue 1, pages 260-268.
881:, volume 36, issue 1, pages 251-259.
712:, volume 28, issue 4, pages 894-900.
381:whose molecule can be described as a
205:Key: RDIDGZFQASQXBU-UHFFFAOYSA-N
7:
480:, which are among the 43 isomers of
135:
691:10.1111/j.1432-1033.1968.tb00328.x
14:
820:R. Criegee and P. Becher (1957):
791:, volume C-61, pages o358-o360.
683:European Journal of Biochemistry
253:
22:
765:, volume 1966, pages 1527-1531.
368:1,2,4,5-tetrahydroxycyclohexane
344:(at 25 °C , 100 kPa).
54:1,2,4,5-Tetrahydroxycyclohexane
259:
247:
1:
752:, volume 34, pages 1159-1162.
738:10.1016/S0008-6215(98)00073-1
598:isomer) by hydroxyla-tion of
319:very highly soluble in water
835:Journal of Organic Chemistry
807:T. Posternak et al. (1955):
710:Journal of Organic Chemistry
778:, volume 46, pages 605-611.
966:
776:Canadian Journal of Botany
748:E.O. von Lippmann (1901),
512:The possible isomers are:
364:cyclohexane-1,2,4,5-tetrol
45:Cyclohexane-1,2,4,5-tetrol
17:1,2,4,5-Cyclohexanetetrol
824:, volume 90, pages 2516-.
797:10.1107/S0108270105011066
685:, volume 5, pages 1-12.
360:1,2,4,5-Cyclohexanetetrol
338:
323:
234:
214:
189:
59:
51:
39:
34:
21:
928:10.1002/hlca.19550380123
907:10.1002/hlca.19530360132
887:10.1002/hlca.19530360131
811:, volume 38, pages 208-.
500:Isomers and nomenclature
920:Helvetica Chimica Acta
899:Helvetica Chimica Acta
879:Helvetica Chimica Acta
809:Helvetica Chimica Acta
789:Acta Crystallographica
504:There are 7 different
730:Carbohydrate Research
659:C2 group (a = 10.675
570:, and its enantiomer.
540:, and its enantiomer.
307:297.1±40.0 estimated
488:, more specifically
41:Preferred IUPAC name
855:Monochrysis lutheri
843:10.1021/jo00249a039
763:Tetrahedron Letters
718:10.1021/jo01039a002
314:Solubility in water
277: g·mol
18:
822:Chemische Berichte
750:Chemische Berichte
600:1,4-cyclohexadiene
478:structural formula
375:-cyclohexanetetrol
348:Infobox references
226:C1C(C(CC(C1O)O)O)O
16:
608:hydrogen peroxide
482:cyclohexanetetrol
356:Chemical compound
354:
353:
158:CompTox Dashboard
101:Interactive image
957:
930:
915:
909:
895:
889:
875:
869:
851:
845:
831:
825:
818:
812:
805:
799:
785:
779:
772:
766:
759:
753:
746:
740:
726:
720:
702:
693:
679:
637:selenium dioxide
630:
629:
628:
620:
619:
484:. They are all
464:
463:
462:
454:
453:
445:
444:
434:
433:
432:
424:
423:
415:
414:
393:substituted for
379:organic compound
276:
261:
255:
249:
242:Chemical formula
182:
181:
166:
164:
148:
137:
123:
103:
79:
26:
19:
965:
964:
960:
959:
958:
956:
955:
954:
935:
934:
933:
916:
912:
896:
892:
876:
872:
867:10.1139/f69-282
852:
848:
832:
828:
819:
815:
806:
802:
786:
782:
773:
769:
760:
756:
747:
743:
727:
723:
703:
696:
680:
673:
669:
627:
624:
623:
622:
618:
615:
614:
613:
611:
577:
502:
476:with this same
468:
461:
458:
457:
456:
452:
449:
448:
447:
443:
440:
439:
438:
436:
431:
428:
427:
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419:
418:
417:
413:
410:
409:
408:
406:
405:can be written
357:
350:
345:
316:
274:
264:
258:
252:
244:
230:
227:
222:
221:
210:
207:
206:
203:
197:
196:
185:
175:DTXSID501312132
167:
160:
151:
138:
126:
106:
93:
82:
69:
55:
47:
46:
30:
27:
12:
11:
5:
963:
961:
953:
952:
947:
937:
936:
932:
931:
910:
890:
870:
846:
826:
813:
800:
780:
767:
754:
741:
721:
694:
670:
668:
665:
625:
616:
604:stoichiometric
576:
573:
572:
571:
561:
551:
541:
531:
501:
498:
466:
459:
450:
441:
429:
420:
411:
355:
352:
351:
346:
342:standard state
339:
336:
335:
334:149.8±21.9 °C
332:
326:
325:
321:
320:
317:
312:
309:
308:
305:
299:
298:
295:
289:
288:
287:1.6±0.1 g/cm3
285:
279:
278:
272:
266:
265:
262:
256:
250:
245:
240:
237:
236:
232:
231:
229:
228:
225:
217:
216:
215:
212:
211:
209:
208:
204:
201:
200:
192:
191:
190:
187:
186:
184:
183:
170:
168:
156:
153:
152:
150:
149:
141:
139:
131:
128:
127:
125:
124:
116:
114:
108:
107:
105:
104:
96:
94:
87:
84:
83:
81:
80:
72:
70:
65:
62:
61:
57:
56:
53:
49:
48:
44:
43:
37:
36:
32:
31:
28:
13:
10:
9:
6:
4:
3:
2:
962:
951:
950:Cyclohexanols
948:
946:
943:
942:
940:
929:
925:
921:
914:
911:
908:
904:
900:
894:
891:
888:
884:
880:
874:
871:
868:
864:
860:
856:
850:
847:
844:
840:
836:
830:
827:
823:
817:
814:
810:
804:
801:
798:
794:
790:
784:
781:
777:
771:
768:
764:
758:
755:
751:
745:
742:
739:
735:
731:
725:
722:
719:
715:
711:
707:
701:
699:
695:
692:
688:
684:
678:
676:
672:
666:
664:
662:
658:
654:
650:
646:
642:
638:
634:
609:
605:
601:
597:
594:
590:
586:
581:
574:
569:
565:
562:
559:
555:
552:
549:
545:
542:
539:
535:
532:
529:
528:
522:
518:
515:
514:
513:
510:
507:
499:
497:
495:
491:
487:
483:
479:
475:
470:
404:
400:
396:
392:
388:
384:
380:
376:
374:
369:
365:
361:
349:
343:
337:
333:
331:
328:
327:
322:
318:
315:
311:
310:
306:
304:
303:Boiling point
301:
300:
296:
294:
293:Melting point
291:
290:
286:
284:
281:
280:
273:
271:
268:
267:
246:
243:
239:
238:
233:
224:
220:
213:
199:
195:
188:
180:
176:
172:
171:
169:
159:
155:
154:
147:
143:
142:
140:
134:
130:
129:
122:
118:
117:
115:
113:
110:
109:
102:
98:
97:
95:
91:
86:
85:
78:
74:
73:
71:
68:
64:
63:
58:
50:
42:
38:
33:
25:
20:
919:
913:
898:
893:
878:
873:
858:
854:
849:
834:
829:
821:
816:
808:
803:
788:
783:
775:
770:
762:
757:
749:
744:
729:
724:
709:
705:
682:
595:
592:
588:
582:
578:
567:
564:1α,2β,4α,5β-
563:
557:
554:1α,2β,4β,5α-
553:
547:
544:1α,2α,4β,5β-
543:
537:
534:1α,2α,4α,5β-
533:
526:
524:
520:
517:1α,2α,4α,5α-
516:
511:
503:
472:There are 7
471:
372:
371:
367:
363:
362:(also named
359:
358:
60:Identifiers
52:Other names
653:sugar beets
585:Ahmet Maras
401:atoms. Its
383:cyclohexane
330:Flash point
235:Properties
939:Categories
667:References
657:monoclinic
606:amount of
560:(achiral).
550:(achiral).
521:1,2,4,5/0-
385:with four
270:Molar mass
112:ChemSpider
88:3D model (
77:35652-37-0
67:CAS Number
641:catalyzer
633:1-butanol
631:, 30% in
583:In 1998,
575:Synthesis
494:cyclitols
635:), with
568:1,2/4,5-
558:1,4/2,5-
548:1,2/4,5-
538:1,2,4/5-
395:hydrogen
387:hydroxyl
377:) is an
324:Hazards
945:Tetrols
649:betitol
645:ethanol
506:isomers
490:tetrols
486:polyols
474:isomers
403:formula
283:Density
275:148.158
133:PubChem
399:carbon
391:groups
219:SMILES
146:546000
121:475253
35:Names
602:with
593:trans
589:trans
523:, or
465:, or
389:(OH)
370:, or
194:InChI
90:JSmol
596:para
525:all-
492:and
455:(OH)
373:para
924:doi
903:doi
883:doi
863:doi
857:".
839:doi
793:doi
734:doi
714:doi
687:doi
639:as
566:or
556:or
546:or
536:or
527:cis
163:EPA
136:CID
941::
708:.
697:^
674:^
519:,
469:.
435:,
421:12
366:,
257:12
926::
905::
885::
865::
841::
795::
736::
716::
689::
661:Å
626:2
621:O
617:2
612:H
610:(
591:-
467:2
460:4
451:8
446:H
442:6
437:C
430:4
425:O
416:H
412:6
407:C
263:4
260:O
254:H
251:6
248:C
165:)
161:(
92:)
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