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2D Structure
Also known as: Myo-inositol, Scyllo-inositol, Epi-inositol, Muco-inositol, Allo-inositol, I-inositol
Molecular Formula
C6H12O6
Molecular Weight
180.16  g/mol
InChI Key
CDAISMWEOUEBRE-UHFFFAOYSA-N
FDA UNII
587A93P465

Myoinositol is a metabolite found in or produced by Saccharomyces cerevisiae.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
cyclohexane-1,2,3,4,5,6-hexol
2.1.2 InChI
InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H
2.1.3 InChI Key
CDAISMWEOUEBRE-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1(C(C(C(C(C1O)O)O)O)O)O
2.2 Other Identifiers
2.2.1 UNII
587A93P465
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. Myo-inositol

2. Scyllo-inositol

3. Epi-inositol

4. Muco-inositol

5. Allo-inositol

6. I-inositol

7. 87-89-8

8. Meso-inositol

9. 1d-chiro-inositol

10. 1l-chiro-inositol

11. Neo-inositol

12. D-(+)-chiro-inositol

13. Cis-inositol

14. 643-12-9

15. 488-59-5

16. D-chiro-inositol

17. Myoinositol

18. Scyllitol

19. 6917-35-7

20. Cyclohexane-1,2,3,4,5,6-hexaol

21. 488-58-4

22. Cyclohexane-1,2,3,4,5,6-hexol

23. Quercinitol

24. Mesoinositol

25. 551-72-4

26. Cocositol

27. Meat Sugar

28. Myoinosite

29. Dambose

30. Chiro-inositol

31. Inositene

32. Inositina

33. L-chiro-inositol

34. Phaseomannite

35. Inosital

36. Inosite

37. Iso-inositol

38. Cyclohexitol

39. Phaseomannitol

40. Inositol, Myo-

41. Mesoinosit

42. Mesoinosite

43. Scyllite

44. Mesovit

45. Nucite

46. Mesol

47. 41546-34-3

48. 643-10-7

49. Cyclohexanehexol

50. 488-55-1

51. Inositol, Meso-

52. Cis-1,2,3,5-trans-4,6-cyclohexanehexol

53. L-inositol

54. D-myo-inositol

55. D-chiro Inositol

56. Bios I

57. Insitolum

58. Isoinositol

59. L-(-)-chiro-inositol

60. (-)-inositol

61. 488-54-0

62. 576-63-6

63. D-inositol

64. L-myo-inositol

65. Inositol, Allo-

66. Inositol, Muco-

67. Inositol, I-

68. Inositol, Scyllo-

69. Inositol (van)

70. Alloinositol

71. Neoinositol

72. Hexahydroxycyclohexane

73. Scyllo-cyclohexanehexol

74. 1d-myo-inositol

75. 1l-myo-inositol

76. Inositol, Cis-

77. Inositol, Epi-

78. Inositol, Neo-

79. Epi-cyclohexanehexol

80. (+)-inositol

81. 1,2,3,4,5,6-cyclohexanehexol

82. (-)-chiro-inositol

83. Elnd005

84. Rat Antispectacled Eye Factor

85. Levoinositol

86. Ccris 6745

87. 1,2,3,5-trans-4,6-cyclohexanehexol, Cis-

88. Azd 103

89. Chiro-inositol, (-)-

90. Inositol, Myo

91. Mfcd00077932

92. 1,3,5/2,4,6-hexahydroxycyclohexane

93. (1r,2r,3r,4r,5s,6s)-cyclohexane-1,2,3,4,5,6-hexaol

94. (1r,2r,3s,4r,5r,6s)-cyclohexane-1,2,3,4,5,6-hexaol

95. (1r,2r,3s,4s,5s,6s)-cyclohexane-1,2,3,4,5,6-hexol

96. 1-l-chiro-inositol

97. Inositol, D-chiro-

98. (+)-chiro-inositol

99. 38876-99-2

100. Chebi:17268

101. Ai3-16111

102. Nsc8101

103. 1,3,5/2,4,6-cyclohexanehexol

104. 1,2,3,5/4,6-cyclohexanehexol

105. Nsc 8101

106. Nsc-8101

107. Chiro-inositol, (+)-

108. (1r,2r,3r,4r,5r,6r)-cyclohexane-1,2,3,4,5,6-hexol

109. (1r,2r,3r,4s,5s,6s)-cyclohexane-1,2,3,4,5,6-hexaol

110. (1r,2r,3s,4s,5s,6s)-cyclohexane-1,2,3,4,5,6-hexaol

111. 1,2,3,4,5,6-hexahydroxy-cyclohexane

112. Nsc-25142

113. Nsc-55551

114. Nsc404118

115. Myo-inositol;meso-inositol

116. Nsc 404118

117. Nsc-404118

118. J101.890f

119. J101.891d

120. (1s,2s,3s,4s,5s,6s)-cyclohexane-1,2,3,4,5,6-hexol

121. 63gqx5qw03

122. 8lq63p85ic

123. 9o6y5o4p9w

124. Elnd-005

125. R1y9f3n15a

126. (1r,2r,3r,4s,5s,6s)-cyclohexane-1,2,3,4,5,6-hexol

127. (1r,2r,3s,4r,5r,6s)-cyclohexane-1,2,3,4,5,6-hexol

128. (1s,2r,3r,4s,5s,6s)-cyclohexane-1,2,3,4,5,6-hexol

129. Chebi:10642

130. Chebi:23927

131. Chebi:27372

132. Chebi:27987

133. Azd-103

134. 4661d3jp8d

135. 6r79wv4r10

136. M94176hj2f

137. Inositol (van8c

138. Nsc45517

139. Nsc55551

140. Nsc55552

141. Nsc-55552

142. Nsc-55558

143. 1vs4x81277

144. Nsc-103959

145. Nsc-127230

146. Ins

147. Ncgc00159409-02

148. (1r,2r,3r,4r,5s,6s)-cyclohexane-1,2,3,4,5,6-hexol

149. (1r,2r,3s,4r,5s,6s)-cyclohexane-1,2,3,4,5,6-hexaol

150. (1r,2r,3s,4s,5r,6s)-cyclohexane-1,2,3,4,5,6-hexol

151. 4l6452s749

152. 587a93p465

153. Inositol, Myo- (8ci)

154. Dsstox_cid_3146

155. Dsstox_rid_76890

156. Dsstox_gsid_23146

157. 1,3,4,5,6-cyclohexanehexol

158. 1,3,5/4,6-cyclohexanehexol

159. (1r,2r,3s,4r,5s,6s)-cyclohexane-1,2,3,4,5,6-hexol

160. 1,2,4/3,5,6-cyclohexanehexol

161. Rel-(1r,2r,3r,4r,5r,6r)-cyclohexane-1,2,3,4,5,6-hexaol

162. Rel-(1r,2r,3s,4r,5s,6s)-cyclohexane-1,2,3,4,5,6-hexaol

163. Mouse Antialopecia Factor

164. 1,2,3,4,5,6-cyclohexanehexol #

165. Cis-1,2,3,4,5,6-cyclohexanehexol

166. Cas-87-89-8

167. Cis-1,3,5-trans-4,6-cyclohexanehexol

168. Smr000857145

169. Smr000857319

170. Smr000857320

171. Inositol Nf 12

172. Elnd 005

173. Sr-05000001655

174. Einecs 201-781-2

175. Mfcd00065455

176. 1,2,3,4,5,6-hexahydroxycyclohexane

177. Inositols

178. Unii-63gqx5qw03

179. Unii-8lq63p85ic

180. Unii-9o6y5o4p9w

181. Unii-r1y9f3n15a

182. An Inositol

183. Inositol [nonspecific Isomer]

184. Unii-4661d3jp8d

185. Unii-6r79wv4r10

186. Unii-m94176hj2f

187. Muscle Sugar

188. Inositol Myo-

189. D-muco-inositol

190. Unii-1vs4x81277

191. Inositol Fcc

192. 4irx

193. Inositol, Chiro-

194. Rac-chiro-inositol

195. Unii-4l6452s749

196. Unii-587a93p465

197. Inosital (tn)

198. Inositol (nf)

199. Cbu

200. Einecs 207-681-5

201. Einecs 207-682-0

202. Einecs 209-000-7

203. Einecs 211-393-5

204. Einecs 211-394-0

205. Einecs 230-024-9

206. Nsc 25142

207. Epiinositol

208. (+)-epi-inositol

209. Chiro-inositols

210. Epi-inositol, 98%

211. Allo-inositol, 97%

212. Inositol [usan:nf]

213. Inositol, Meso

214. Spectrum_001595

215. 2os9

216. Inositol [inci]

217. Inositol [usan]

218. Inositol [fcc]

219. Inositol [inn]

220. Orthorhombic Myo-inositol

221. D-(+)-chiro Inositol

222. Dl-chiro-inositol

223. Inositol [mi]

224. Inositol (d)

225. Inositol (l)

226. Inositol [vandf]

227. Spectrum3_001053

228. Spectrum4_001193

229. Spectrum5_000961

230. Myo-inositol, >=99%

231. Inositol [mart.]

232. Bmse000102

233. Bmse000103

234. Bmse000113

235. Bmse000901

236. Bmse000922

237. Epitope Id:144993

238. Inositol [usp-rs]

239. Inositol [who-dd]

240. Scyllo-inositol, >=98%

241. Schembl5831

242. Schembl5832

243. Schembl5969

244. Nciopen2_008191

245. Bspbio_002606

246. Kbiogr_001885

247. Kbioss_002075

248. Mls001332377

249. Mls001332378

250. Mls001335965

251. Mls001335966

252. Mls001335967

253. Mls001335968

254. Schembl187278

255. Schembl187397

256. Schembl187796

257. Schembl188106

258. Schembl188237

259. Schembl491333

260. Schembl959404

261. Schembl959405

262. Chembl278373

263. Chembl468154

264. Gtpl4495

265. Gtpl4645

266. Gtpl4648

267. Gtpl4649

268. Megxp0_001817

269. Schembl1055883

270. Schembl4748543

271. Schembl6378921

272. Schembl6468882

273. Schembl6791918

274. Chembl1222251

275. Chembl1231671

276. Chembl1950780

277. Chembl3976780

278. Dtxsid7023146

279. Schembl12371461

280. Schembl12377889

281. Schembl12411898

282. Schembl12711208

283. Schembl12735687

284. Schembl13058696

285. Schembl13114115

286. Schembl13114116

287. Schembl13114128

288. Schembl13207905

289. Schembl13580047

290. Schembl14542470

291. Schembl21388397

292. Acon1_002457

293. Chebi:22357

294. Chebi:23311

295. Chebi:24848

296. Chebi:25492

297. Chebi:27374

298. D-(+)-chiro-inositol, 95%

299. Kbio2_002075

300. Kbio2_004643

301. Kbio2_007211

302. Kbio3_001826

303. L-(-)-chiro-inositol, 95%

304. Dtxsid30110000

305. Dtxsid50905091

306. Myo-inositol, P.a., 98.0%

307. 1,2,3,4,5/6-cyclohexanehexol

308. 1,2,3,4/5,6-cyclohexanehexol

309. 1,2,3/4,5,6-cyclohexanehexol

310. 1,2,4,5/3,6-cyclohexanehexol

311. Dtxsid101028818

312. Dtxsid101028820

313. Dtxsid201028823

314. Dtxsid301028826

315. Dtxsid601028825

316. Dtxsid901028824

317. Hms2091n13

318. Hms2230n03

319. Hms2235h05

320. Hms2235m23

321. Hms3369b06

322. Hms3369f20

323. Hms3373e05

324. Pharmakon1600-01500352

325. D-chiro-inositol [usp-rs]

326. D-chiro-inositol [who-dd]

327. 1,2,3,4,5,6-cyclohexanehexaol

328. Bcp25172

329. Hy-b1411

330. Hy-n3021

331. Myo-inositol [ep Monograph]

332. Nsc25142

333. Nsc55558

334. Zinc1530357

335. D-myo-inositol, Cell Culture Grade

336. Tox21_111642

337. Tox21_302035

338. Ccg-36096

339. Cis-inositol, >=98.0% (tlc)

340. Mfcd00003863

341. Mfcd00272608

342. Mfcd00799555

343. Mfcd00799556

344. Mfcd01321249

345. Nsc 55552

346. Nsc 55558

347. Nsc-45517

348. Nsc103959

349. Nsc127230

350. Nsc757076

351. S4530

352. Stl453612

353. Epi-inositol, >=98.0% (hplc)

354. 1,2,3,4,5,6/0-cyclohexanetetrol

355. Akos006240678

356. Akos006332036

357. Akos015895894

358. Akos015912905

359. Akos015912934

360. Akos015960429

361. Akos015960633

362. Akos015994742

363. Akos024318869

364. Tox21_111642_1

365. Zinc100018867

366. Zinc100019018

367. Zinc100024490

368. Zinc100032893

369. Zinc100035580

370. Zinc100037751

371. Zinc100055570

372. Zinc100073149

373. Zinc100513675

374. Zinc101185827

375. Zinc102201844

376. Zinc103574430

377. Zinc103574467

378. Zinc103574475

379. Zinc250615063

380. Zinc253837650

381. Zinc306121118

382. Cs-4782

383. Cs-w010757

384. Db03106

385. Db13178

386. Db15350

387. Hy-w010041

388. J9.771c

389. Ks-1284

390. Ks-1420

391. Nsc 103959

392. Nsc 127230

393. Nsc-757076

394. Sb44732

395. Sb45039

396. Sb46764

397. Sb46855

398. D-chiro-inositol, >=98.0% (hplc)

399. Ncgc00159409-03

400. Ncgc00159409-04

401. Ncgc00169828-01

402. Ncgc00178580-01

403. Ncgc00178580-03

404. Ncgc00255362-01

405. Ac-11070

406. As-10616

407. As-68396

408. As-68424

409. Cyclohexane-1r,2r,3s,4s,5r,6s-hexol

410. Ls-13189

411. Nci60_041778

412. Sy060836

413. Myo-inositol, Purum, >=98.0% (hplc)

414. Rac-chiro-1,2,3,4,5,6-cyclohexanehexol

415. Sbi-0051369.p003

416. Cis-1,2,4-trans-3,5,6-cyclohexanehexol

417. Db-051583

418. Db-051584

419. Db-054642

420. Hy-121962

421. J101.888d

422. J101.889b

423. J101.892b

424. Myo-inositol, For Microbiology, >=99.0%

425. Cs-0023004

426. Cs-0083766

427. Cs-0369552

428. Ft-0627237

429. Ft-0632208

430. Ft-0632209

431. Ft-0632730

432. Ft-0652045

433. Ft-0670351

434. Ft-0670357

435. Ft-0693444

436. Ft-0693614

437. I0040

438. I0628

439. I0629

440. I0630

441. I0631

442. I0632

443. I0633

444. S6176

445. Myo-inositol, Bioultra, >=99.5% (hplc)

446. Myo-inositol, Saj Special Grade, >=99.0%

447. Myo-inositol, Vetec(tm) Reagent Grade, 99%

448. C00137

449. C06151

450. C06152

451. C06153

452. C19891

453. D08079

454. D78450

455. D91187

456. D91188

457. D91189

458. E78671

459. F19572

460. I-6500

461. M01914

462. T72516

463. Ab00051982_13

464. 643c129

465. A834712

466. A836375

467. A866896

468. Q407997

469. Q743661

470. Q-201583

471. Q2838375

472. Q2974313

473. Q3011024

474. Q3023527

475. Q3205874

476. Q3331426

477. Q3347078

478. Q3589114

479. Sr-05000001655-1

480. Sr-05000001655-5

481. W-202861

482. W-202862

483. W-203081

484. W-203168

485. W-203392

486. 1,2,4/3,5,6-cyclohexane-1,2,3,4,5,6-hexol

487. 7b0cef84-d9ce-4a88-aa7d-ec50c89387a5

488. 1d7a27bf-6060-4fa9-ac46-3bd18dba406e

489. 220128f1-89bf-442d-ad6d-e6d1ea7ba625

490. (1r,2r,3r,4r,5r,6r)-cyclohexane-1,2,3,4,5,6-hexaol

491. (1r,2s,3r,4r,5s,6r)-cyclohexane-1,2,3,4,5,6-hexol

492. (1r,2s,3r,4r,5s,6s)-cyclohexane-1,2,3,4,5,6-hexol

493. D-myo-inositol-1,2,5,6-tetraphosphate Sodium Salt

494. Inositol, United States Pharmacopeia (usp) Reference Standard

495. Myo-inositol, European Pharmacopoeia (ep) Reference Standard

496. (1r,2r,3s,4s,5s,6r)-cyclohexane-1,2,3,4,5,6-hexol

497. 1,2,3,4,5,6-cyclohexanehexol, (cis,cis,cis,trans,cis,trans)- #

498. 1,2,3,4,5,6-cyclohexanehexol, (1alpha,2alpha,3alpha,4beta,5alpha,6beta)

499. Inositol, Pharmaceutical Secondary Standard; Certified Reference Material

500. 1.alpha.,2.alpha.,3.beta.,4.alpha.,5.beta.,6.beta.-cyclohexanehexol

501. 2h3

502. Myo-inositol, Bioreagent, Suitable For Cell Culture, Suitable For Insect Cell Culture, Suitable For Plant Cell Culture

503. Myo-inositol, Pharmagrade, Meets Fcc Testing Specifications, Manufactured Under Appropriate Controls For Use As A Raw Material In Pharma Or Biopharmaceutical Production.

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 180.16 g/mol
Molecular Formula C6H12O6
XLogP3-3.7
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count6
Rotatable Bond Count0
Exact Mass180.06338810 g/mol
Monoisotopic Mass180.06338810 g/mol
Topological Polar Surface Area121 Ų
Heavy Atom Count12
Formal Charge0
Complexity104
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Inositol may be used in food without any limitation. As a drug, inositol is used as a nutrient supplement in special dietary foods and infant formula. As it presents a relevant role in ensuring oocyte fertility, inositol has been studied for its use in the management of polycystic ovaries. Inositol is also being researched for the treatment of diabetes, prevention of metabolic syndrome, aid agent for weight loss, treatment of depression, psychiatric disorder and anxiety disorder and for prevention of cancer.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Inositol can stimulate glucose uptake in skeletal muscle cells which allows the decrease in blood sugar levels. This effect is later seen as a reduction in urine glucose concentration and indicates a decrease in high blood sugar levels. In PCOS, the administration of inositol has produced the remission of symptoms as well as a reduction in male hormone secretion, a regulation of the cholesterol level, and a more efficient fat breakdown which allow to a significant reduction on body mass and appetite. In the cases of infertility, inositol has been proven to increase sperm count and motility, as well as increase the overall quality of oocytes and embryos. In the brain, inositol has been shown to produce an increase in serotonin receptor sensitivity. This activity produces an increase in GABA release. Some of the effects observed in the brain produced a relief in symptoms of anxiety and obsessive-compulsive disorders. In high doses, it has been shown to even reduce panic attacks. In cancer research, inositol has gained interest as it can act as an antioxidant, anti-inflammatory and it seems to enhance immune properties.


5.2 ATC Code

A - Alimentary tract and metabolism

A11 - Vitamins

A11H - Other plain vitamin preparations

A11HA - Other plain vitamin preparations

A11HA07 - Inositol


5.3 Absorption, Distribution and Excretion

Absorption

Inositol is absorbed from the small intestine. In patients with inositol deficiency, the maximal plasma concentration after oral administration of inositol is registered to be of 4 hours. Inositol is taken up by the tissues via sodium-dependent inositol co-transporter which also mediates glucose uptake. Oral ingestion of inositol is registered to generate a maximal plasma concentration of 36-45 mcg.


Route of Elimination

Most of the administered dose is excreted in urine.


Volume of Distribution

The pharmacokinetic profile of inositol was studied in preterm infants and the estimated volume of distribution was reported to be 0.5115 L/kg.


Clearance

The pharmacokinetic profile of inositol was studied in preterm infants and the estimated clearance rate was reported to be 0.0679 L.kg/h.


5.4 Metabolism/Metabolites

It is thought that inositol is metabolized to phosphoinositol and then converted to phosphatylinositol-4,5-biphosphate which is a precursor of the second-messenger molecules. Inositol can be transformed to D-chiro-inositol via the actions of an epimerase. The normal modifications to inositol structure seem to be between all the different isomers.


5.5 Biological Half-Life

The pharmacokinetic profile of inositol was studied in preterm infants and the estimated elimination half-life was reported to be of 5.22 hours.


5.6 Mechanism of Action

The mechanism of action of inositol in brain disorders is not fully understood but it is thought that it may be involved in neurotransmitter synthesis and it is a precursor to the phosphatidylinositol cycle. The change that occurs in the cycle simulates when the postsynaptic receptor is activated but without activating the receptor. This activity provokes a fake activation which regulated the activity of monoamines and other neurotransmitters. Reports have shown that insulin resistance plays a key role in the clinical development of PCOS. The presence of hyperinsulinemia can induce an excess in androgen production by stimulating ovaries to produce androgens and by reducing the sex hormone binding globulin serum levels. One of the mechanisms of insulin deficiency is thought to be related to a deficiency in inositol in the inositolphosphoglycans. The administration of inositol allows it to act as a direct messenger of the insulin signaling and improves glucose tissue uptake. This mechanism is extrapolated to its functions in diabetes treatment, metabolic syndrome, and weight loss. In cancer, the mechanism of action of inositol is not fully understood. It is hypothesized that the administration of inositol increases the level of lower-phosphate inositol phosphates why can affect cycle regulation, growth, and differentiation of malignant cells. On the other hand, the formation of inositol hexaphosphate after administration of inositol presents antioxidant characteristics by the chelation of ferric ions and suppression of hydroxyl radicals.