20:
186:
Furthermore, the hydrogen and the hydroxyl on each carbon atom may lie in two possible arrangements relative to the local ring plane; so that each structural isomer may exist in several
421:
183:, depending on the position of the hydroxyls along the ring. For example, cyclohexanetriol exists in three distinct isomers (1,2,3-, 1,2,4-, and 1,3,5-).
494:
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".
514:
Th. Posternak, D. Reymond, W. Haerdi (1955): "Recherches dans la série des cyclitols XX. Chromatographie sur papier de cyclitols et de cycloses".
190:, depending on which side of the ring plane the hydroxyls are. For example, there are nine stereoisomers of 1,2,3,4,5,6-cyclohexanehexol (
356:
351:
384:
389:
470:
J. S. Craigie (1969): "Some
Salinity-Induced Changes in Growth, Pigments, and Cyclohexanetetrol Content of
450:
CON and CBN IUPAC Commissions on
Nomenclature (1968): "The Nomenclature of Cyclitols - Tentative Rules".
368:
19:
380:
51:, each attached to a different ring carbon atom. The general formula for an unsubstituted cyclitol is
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168:
553:
228:
180:
36:
179:
Unsubstituted cyclitols with the same ring size and number of hydroxyls may exist in several
519:
499:
479:
455:
435:
141:
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376:
140:
The name is also used for compounds that can be viewed as result of substituting various
159:
which are formed in a plant as a response to salt or water stress. Some cyclitols (e.g.
459:
341:; (1R,2S,3r,4R,5S,6s)-cyclohexane-1,2,3,4,5,6-hexayl hexakis; inositol hexakisphosphate
156:
547:
402:
296:
164:
431:
280:
187:
426:
338:
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273:; (1R,2R,3R,4S,5R,6S)-3,6-dimethoxycyclohexane-1,2,4,5-tetraol; di-O-methyl-(+)-
270:
160:
149:
44:
311:(1R,2S,3R,4S,5R,6S)-5,6-dimethoxycyclohexane-1,2,3,4-tetraol; 1,2-di-O-methyl-
308:
240:
216:
195:
523:
430:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
439:
325:
243:; (1R,2R,3S,4S,5R,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol; D-(−)-O-methyl-
302:
263:; (1R,2S,3S,4S,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentaol; 4-O-methyl-
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222:
191:
145:
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503:
148:
atoms in such a molecule, as well as similar molecules with one or more
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225:, or cyclohexane-1,2,3,4,5,6-hexol; four out of nine possible isomers.
483:
253:; (1S,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol; 3-O-methyl-D-
219:, or cyclohex-5-ene-1,2,3,4-tetrol; two out of ten possible isomers.
283:; (1R,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol; 2-0-methyl-
199:
18:
305:; (1S,2S,3S,4R)-5-(Hydroxymethyl)cyclohex-5-ene-1,2,3,4-tetrol
293:; (1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid
299:; (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
31:=4). There are actually 10 isomers with this same structure.
202:
has provided a nomenclature for cyclitol stereoisomers.
375:
in various solvents, and three methods of development:
371:
and others described the separation of cyclitols by
476:Journal of the Fisheries Research Board of Canada
539:List of cyclitol molecules on chemicalland21.com
155:Cyclitols and their derivatives are some of the
8:
498:, volume 53, issue 14, pages 3338-3342.
478:, volume 26, issue 11, pages 2959-2967.
23:The cyclitol 1,2,3,4-cyclohexanetetrol (
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7:
518:volume 38, issue 1, pages 191-194
460:10.1111/j.1432-1033.1968.tb00328.x
427:Compendium of Chemical Terminology
14:
452:European Journal of Biochemistry
1:
393:followed by Tollens reagent.
206:Naturally occurring cyclitols
496:Journal of Organic Chemistry
357:1,2,3,4,5-Cyclopentanepentol
16:Class of chemical compounds
570:
175:Isomerism and nomenclature
47:containing at least three
454:, volume 5, pages 1-12.
352:1,2,3,4-Cyclohexanetetrol
328:, a pinitol digalactoside
524:10.1002/hlca.19550380122
385:Scherer-Gallois reaction
440:10.1351/goldbook.C01493
194:), and two of them are
516:Helvetica Chimica Acta
390:Acetobacter suboxydans
32:
22:
387:), and digestion by
373:paper chromatography
169:hydrolysable tannins
504:10.1021/jo00249a039
472:Monochrysis lutheri
181:structural isomers
157:compatible solutes
33:
229:Cyclohexanetetrol
142:functional groups
37:organic chemistry
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381:Meillère reagent
377:Tollens reagents
363:Analysis methods
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346:Other cyclitols
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533:External links
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403:Aminocyclitol
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211:Unsubstituted
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188:stereoisomers
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165:shikimic acid
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152:in the ring.
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281:Quebrachitol
274:
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150:double bonds
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339:Phytic acid
291:Quinic acid
271:Pinpollitol
235:Substituted
196:enantiomers
45:cycloalkane
409:References
333:Phosphates
320:Glycosides
309:Viscumitol
241:Bornesitol
217:Conduritol
129:where 3 ≤
554:Cyclitols
432:Cyclitols
369:Posternak
367:In 1955,
326:Ciceritol
315:-inositol
287:-inositol
277:-inositol
267:-inositol
257:-inositol
247:-inositol
548:Category
397:See also
303:Valienol
261:Ononitol
223:Inositol
192:inositol
146:hydrogen
144:for the
49:hydroxyl
41:cyclitol
251:Pinitol
379:, the
198:. The
161:quinic
422:IUPAC
285:chiro
275:chiro
255:chiro
200:IUPAC
43:is a
313:muco
80:(OH)
39:, a
27:=6,
520:doi
500:doi
480:doi
474:".
456:doi
436:doi
434:".
265:myo
245:myo
163:or
92:or
35:In
550::
424:,
171:.
137:.
133:≤
522::
502::
482::
458::
438::
135:n
131:x
123:x
117:O
112:n
110:2
105:H
100:n
94:C
86:x
75:x
73:-
71:n
69:2
64:H
59:n
53:C
29:x
25:n
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