Inositol

Base Information

• Chemical Name: Inositol
• CAS No.: 87-89-8
• Deprecated CAS: 53319-35-0,887751-76-0,36190-90-6,19030-27-4,173524-45-3
• Molecular Formula: C6H12O6
• Molecular Weight: 180.158
• Hs Code.: 2906.13
• European Community (EC) Number: 201-781-2,211-394-0,230-024-9,207-682-0,207-681-5,209-000-7,211-393-5,610-437-4
• NSC Number: 757076,404118,127230,103959,55558,55552,55551,45517,25142,8101
• UNII: 8LQ63P85IC,63GQX5QW03,9O6Y5O4P9W,M94176HJ2F,R1Y9F3N15A,6R79WV4R10,1VS4X81277,4L6452S749,4661D3JP8D,587A93P465
• DSSTox Substance ID: DTXSID7023146,DTXSID30110000,DTXSID101028818,DTXSID101028820,DTXSID201028823,DTXSID301028826,DTXSID50905091,DTXSID601028825,DTXSID901028824
• Nikkaji Number: J4.282J,J522.945F,J9.771C,J92.778C,J101.888D,J101.889B,J101.890F,J101.891D,J101.892B
• Wikipedia: Inositol,Allo-Inositol,1D-chiro-Inositol,Scyllo-Inositol,Neo-Inositol,Muco-Inositol,1L-chiro-Inositol,Epi-Inositol,Cis-Inositol
• Wikidata: Q407997,Q2838375,Q3011024,Q743661,Q3023527,Q3205874,Q3347078,Q3331426,Q3589114,Q2974313
• NCI Thesaurus Code: C122987,C28163,C189814
• RXCUI: 5833
• Metabolomics Workbench ID: 49811
• ChEMBL ID: CHEMBL468154,CHEMBL1950780,CHEMBL1231671,CHEMBL1222251,CHEMBL278373,CHEMBL3976780
• Mol file: 87-89-8.mol

Synonyms:inositol;myo-inositol;Scyllo-inositol;epi-Inositol;Muco-Inositol;Allo-inositol;i-Inositol;87-89-8;meso-Inositol;Neo-inositol;1D-Chiro-inositol;1L-Chiro-inositol;D-(+)-chiro-Inositol;cis-Inositol;643-12-9;488-59-5;D-chiro-Inositol;Myoinositol;Scyllitol;6917-35-7;Cyclohexane-1,2,3,4,5,6-hexaol;488-58-4;cyclohexane-1,2,3,4,5,6-hexol;Quercinitol;mesoinositol;Cocositol;551-72-4;Meat sugar;Myoinosite;Dambose;chiro-inositol;Inositene;Inositina;L-chiro-Inositol;Phaseomannite;Inosital;Inosite;Iso-inositol;Cyclohexitol;Phaseomannitol;41546-34-3;Inositol, myo-;Mesoinosit;Mesoinosite;Scyllite;Mesovit;Nucite;Mesol;643-10-7;488-55-1;Cyclohexanehexol;Inositol, meso-;cis-1,2,3,5-trans-4,6-Cyclohexanehexol;D-myo-Inositol;D-chiro Inositol;488-54-0;Bios I;Insitolum;Isoinositol;L-(-)-chiro-Inositol;(-)-Inositol;576-63-6;d-Inositol;L-Inositol;L-myo-Inositol;Inositol, allo-;Inositol, muco-;Inositol, i-;Inositol, scyllo-;Inositol (VAN);alloinositol;neoinositol;Hexahydroxycyclohexane;scyllo-Cyclohexanehexol;1D-myo-Inositol;1L-myo-Inositol;Inositol, cis-;Inositol, epi-;Inositol, neo-;epi-Cyclohexanehexol;(+)-Inositol;1,2,3,4,5,6-Cyclohexanehexol;(-)-chiro-Inositol;ELND005;Rat antispectacled eye factor;Levoinositol;CCRIS 6745;1,2,3,5-trans-4,6-Cyclohexanehexol, cis-;Mouse antialopecia factor;AZD 103;Chiro-inositol, (-)-;Inositol, myo;(1R,2R,3S,4R,5r,6S)-cyclohexane-1,2,3,4,5,6-hexaol;38876-99-2;MFCD00077932;(1r,2r,3r,4r,5r,6r)-cyclohexane-1,2,3,4,5,6-hexol;1,3,5/2,4,6-Hexahydroxycyclohexane;(1R,2R,3R,4R,5S,6S)-Cyclohexane-1,2,3,4,5,6-hexaol;(1R,2R,3S,4S,5S,6S)-Cyclohexane-1,2,3,4,5,6-hexaol;1-L-chiro-Inositol;Inositol, D-chiro-;ELND 005;(+)-Chiro-Inositol;CHEBI:17268;AI3-16111;NSC8101;1,3,5/2,4,6-cyclohexanehexol;1,2,3,5/4,6-Cyclohexanehexol;NSC 8101;NSC-8101;Chiro-inositol, (+)-;(1r,2R,3S,4r,5R,6S)-cyclohexane-1,2,3,4,5,6-hexol;EINECS 201-781-2;(1R,2R,3R,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexaol;(1R,2R,3S,4S,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol;1,2,3,4,5,6-HEXAHYDROXY-CYCLOHEXANE;NSC-25142;NSC-55551;NSC404118;myo-Inositol;NSC 404118;NSC-404118;UNII-63GQX5QW03;UNII-8LQ63P85IC;UNII-9O6Y5O4P9W;UNII-R1Y9F3N15A;Inositol [Nonspecific isomer];UNII-4661D3JP8D;UNII-6R79WV4R10;UNII-M94176HJ2F;J101.890F;J101.891D;(1s,2s,3s,4s,5s,6s)-cyclohexane-1,2,3,4,5,6-hexol;63GQX5QW03;8LQ63P85IC;9O6Y5O4P9W;ELND-005;R1Y9F3N15A;(1R,2R,3R,4R,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol;(1r,2R,3R,4s,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol;(1s,2R,3R,4s,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol;DTXSID7023146;UNII-1VS4X81277;CHEBI:10642;CHEBI:23927;CHEBI:27372;CHEBI:27987;AZD-103;4661D3JP8D;6R79WV4R10;M94176HJ2F;UNII-4L6452S749;UNII-587A93P465;Inositol (NF);Inositol (VAN8C;Inositol [NF];NSC45517;NSC55551;NSC55552;EINECS 207-681-5;EINECS 207-682-0;EINECS 209-000-7;EINECS 211-393-5;EINECS 211-394-0;EINECS 230-024-9;NSC 25142;NSC-55552;NSC-55558;1VS4X81277;NSC-103959;NSC-127230;INS;NCGC00159409-02;(1R,2R,3S,4R,5S,6S)-cyclohexane-1,2,3,4,5,6-hexaol;(1R,2R,3S,4R,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol;(1r,2R,3S,4s,5R,6S)-cyclohexane-1,2,3,4,5,6-hexol;4L6452S749;587A93P465;Inositol, myo- (8CI);MYO-INOSITOL-1,2,3,4,5,6-D6;1,3,4,5,6-Cyclohexanehexol;1,3,5/4,6-Cyclohexanehexol;DTXCID2065254;1,2,4/3,5,6-cyclohexanehexol;rel-(1r,2r,3r,4r,5r,6r)-Cyclohexane-1,2,3,4,5,6-hexaol;rel-(1R,2r,3S,4R,5s,6S)-Cyclohexane-1,2,3,4,5,6-hexaol;1,2,3,4,5,6-Cyclohexanehexol #;cis-1,2,3,4,5,6-cyclohexanehexol;CAS-87-89-8;cis-1,3,5-trans-4,6-Cyclohexanehexol;SMR000857145;SMR000857319;SMR000857320;Inositol NF 12;SR-05000001655;MFCD00065455;1,2,3,4,5,6-Hexahydroxycyclohexane;inositols;an inositol;Mio-inositol;Muscle sugar;inositol myo-;Myo- inositol;Inositol FCC;4irx;Inositol, chiro-;rac-chiro-inositol;Inosital (TN);CBU;EPIINOSITOL;(+)-Epi-Inositol;CHIRO-INOSITOLS;Epi-inositol, 98%;allo-Inositol, 97%;Inositol [USAN:NF];INOSITOL, MESO;Spectrum_001595;2os9;INOSITOL [INCI];INOSITOL [USAN];D-( )-chiro-Inositol;INOSITOL [FCC];INOSITOL [INN];orthorhombic myo-inositol;D-(+)-Chiro Inositol;DL-CHIRO-INOSITOL;INOSITOL [MI];INOSITOL (D);INOSITOL (L);INOSITOL [VANDF];Spectrum3_001053;Spectrum4_001193;Spectrum5_000961;myo-Inositol, >=99%;INOSITOL [MART.];bmse000102;bmse000103;bmse000113;bmse000901;bmse000922;D03SHD;D07CPO;D08DXZ;D0B1EY;D0Y4UQ;Epitope ID:144993;INOSITOL [USP-RS];INOSITOL [WHO-DD];scyllo-Inositol, >=98%;SCHEMBL5831;SCHEMBL5832;SCHEMBL5969;NCIOpen2_008191;BSPBio_002606;KBioGR_001885;KBioSS_002075;MLS001332377;MLS001332378;MLS001335965;MLS001335966;MLS001335967;MLS001335968;SCHEMBL187278;SCHEMBL187397;SCHEMBL187796;SCHEMBL188106;SCHEMBL188237;SCHEMBL491333;SCHEMBL959404;SCHEMBL959405;CHEMBL278373;CHEMBL468154;GTPL4495;GTPL4645;GTPL4648;GTPL4649;MEGxp0_001817;SCHEMBL1055883;SCHEMBL4748543;SCHEMBL6378921;SCHEMBL6468882;SCHEMBL6791918;CHEMBL1222251;CHEMBL1231671;CHEMBL1950780;CHEMBL3976780;SCHEMBL12371461;SCHEMBL12377889;SCHEMBL12411898;SCHEMBL12711208;SCHEMBL12735687;SCHEMBL13058696;SCHEMBL13114115;SCHEMBL13114116;SCHEMBL13114128;SCHEMBL13207905;SCHEMBL13580047;SCHEMBL14542470;SCHEMBL21388397;ACon1_002457;CHEBI:22357;CHEBI:23311;CHEBI:24848;CHEBI:25492;CHEBI:27374;D-(+)-chiro-Inositol, 95%;KBio2_002075;KBio2_004643;KBio2_007211;KBio3_001826;L-(-)-chiro-Inositol, 95%;AXD 103;DTXSID30110000;DTXSID50905091;myo-Inositol, p.a., 98.0%;1,2,3,4,5/6-cyclohexanehexol;1,2,3,4/5,6-cyclohexanehexol;1,2,3/4,5,6-cyclohexanehexol;1,2,4,5/3,6-cyclohexanehexol;DTXSID101028818;DTXSID101028820;DTXSID201028823;DTXSID301028826;DTXSID601028825;DTXSID901028824;HMS2091N13;HMS2230N03;HMS2235H05;HMS2235M23;HMS3369B06;HMS3369F20;HMS3373E05;Pharmakon1600-01500352;D-CHIRO-INOSITOL [USP-RS];D-CHIRO-INOSITOL [WHO-DD];1,2,3,4,5,6-Cyclohexanehexaol;BCP25172;HY-B1411;HY-N3021;MYO-INOSITOL [EP MONOGRAPH];NSC25142;NSC55558;D-myo-Inositol, Cell Culture Grade;Tox21_111642;Tox21_302035;CCG-36096;cis-Inositol, >=98.0% (TLC);MFCD00003863;MFCD00272608;MFCD00799555;MFCD00799556;MFCD01321249;NSC 55552;NSC 55558;NSC-45517;NSC103959;NSC127230;NSC757076;s4530;STL453612;epi-Inositol, >=98.0% (HPLC);1,2,3,4,5,6/0-cyclohexanetetrol;AKOS006240678;AKOS006332036;AKOS015895894;AKOS015912905;AKOS015912934;AKOS015960429;AKOS015960633;AKOS015994742;AKOS024318869;Tox21_111642_1;CS-4782;CS-W010757;CS-W017225;DB03106;DB13178;DB15350;HY-W010041;HY-W016509;HY-W021265;HY-W127726;J9.771C;KS-1284;KS-1420;LS-2350;NSC 103959;NSC 127230;NSC-757076;SB44732;SB45039;SB46764;SB46855;D-chiro-Inositol, >=98.0% (HPLC);NCGC00159409-03;NCGC00159409-04;NCGC00169828-01;NCGC00178580-01;NCGC00178580-03;NCGC00255362-01;AC-11070;AS-10616;AS-68396;AS-68424;cyclohexane-1R,2R,3S,4S,5R,6S-hexol;NCI60_041778;SY060836;myo-Inositol, purum, >=98.0% (HPLC);rac-chiro-1,2,3,4,5,6-cyclohexanehexol;SBI-0051369.P003;cis-1,2,4-trans-3,5,6-Cyclohexanehexol;HY-121962;J101.888D;J101.889B;J101.892B;myo-Inositol, for microbiology, >=99.0%;CS-0023004;CS-0039882;CS-0083766;CS-0185922;CS-0369552;FT-0627237;FT-0632208;FT-0632209;FT-0632730;FT-0652045;FT-0670351;FT-0670357;FT-0693444;FT-0693614;I0040;I0628;I0629;I0630;I0631;I0632;I0633;S6176;EN300-82941;myo-Inositol, BioUltra, >=99.5% (HPLC);myo-Inositol, SAJ special grade, >=99.0%;myo-Inositol, Vetec(TM) reagent grade, 99%;C00137;C06151;C06152;C06153;C19891;D08079;D78450;D91187;D91188;D91189;E78671;EN300-658805;F19572;I-6500;M01914;T72516;AB00051982_13;EN300-7361851;EN300-7411506;A834712;A836375;A866896;EN300-19631206;EN300-19632288;EN300-25914216;Q407997;Q743661;Q-201583;Q2838375;Q2974313;Q3011024;Q3023527;Q3205874;Q3331426;Q3347078;Q3589114;SR-05000001655-1;SR-05000001655-5;W-202861;W-202862;W-203081;W-203168;W-203392;1,2,4/3,5,6-Cyclohexane-1,2,3,4,5,6-hexol;7B0CEF84-D9CE-4A88-AA7D-EC50C89387A5;1D7A27BF-6060-4FA9-AC46-3BD18DBA406E;220128F1-89BF-442D-AD6D-E6D1EA7BA625;Z1486007281;(1r,2r,3r,4r,5r,6r)-cyclohexane-1,2,3,4,5,6-hexaol;(1R,2S,3r,4R,5S,6r)-cyclohexane-1,2,3,4,5,6-hexol;(1R,2S,3r,4R,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol;(1R,2S,3s,4R,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol;Inositol, United States Pharmacopeia (USP) Reference Standard;myo-Inositol, European Pharmacopoeia (EP) Reference Standard;(1R,2R,3S,4S,5S,6R)-CYCLOHEXANE-1,2,3,4,5,6-HEXOL;1,2,3,4,5,6-Cyclohexanehexol, (cis,cis,cis,trans,cis,trans)- #;1,2,3,4,5,6-cyclohexanehexol, (1alpha,2alpha,3alpha,4beta,5alpha,6beta);Inositol, Pharmaceutical Secondary Standard;Certified Reference Material;1.ALPHA.,2.ALPHA.,3.BETA.,4.ALPHA.,5.BETA.,6.BETA.-CYCLOHEXANEHEXOL;173524-45-3;2H3;myo-Inositol, BioReagent, suitable for cell culture, suitable for insect cell culture, suitable for plant cell culture

Chemical Property of Inositol

Chemical Property:

• Appearance/Colour: white powder
• Melting Point: 222-227 °C(lit.)
• Refractive Index: 1.6170 (estimate)
• Boiling Point: 291.326 °C at 760 mmHg
• PKA: 12.63±0.70(Predicted)
• Flash Point: 143.387 °C
• PSA: 121.38000
• Density: 2.039 g/cm³
• LogP: -3.83460
• Storage Temp.: Store at RT.
• Solubility.: H2O: 0.5 M at 20 °C, clear, colorless
• Water Solubility.: 14 g/100 mL (25 ºC)
• XLogP3: -3.7
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 180.06338810
• Heavy Atom Count: 12
• Complexity: 104

Purity/Quality:

97%min ^*data from raw suppliers

Inositol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Monosaccharides and Derivatives
• Canonical SMILES: C1(C(C(C(C(C1O)O)O)O)O)O
• Recent ClinicalTrials: Inositol Treatment in Different Type of PCOS Phenotype
• Recent EU Clinical Trials: A 36-Week Safety Extension Study of Oral ELND005 for Treatment of Agitation and Aggression in Patients With Moderate to Severe Alzheimer's Disease.
• History: Inositol was first isolated in 1850 by the German physician and chemist Johann Joseph Scherer. It was named "inositol" due to its sweet taste and its isolation from muscle cells.
• Biological Significance: Inositols, especially myo-inositol and inositol hexakisphosphate (IP6 or phytic acid), are widely distributed among plants and mammalian cells. They play crucial roles in biology and signaling of eukaryotic cells.
• Structural Isomers: There are nine possible stereoisomers of inositol, with myo-inositol being the most studied. Other naturally occurring isomers include scyllo-, muco-, neo-, and d-chiro-inositols.
• Physiological Functions: Myo-inositol is involved in various cellular functions, including the development and function of peripheral nerves, osteogenesis, and reproduction. It has been implicated in counteracting cancer and metabolic disorders such as polycystic ovary syndrome (PCOS), gestational diabetes mellitus (GDM), infertility, and thyroid disorders.
• Insulin Sensitivity: Orally administered myo-inositol and its isomer chiro-inositol have been shown to facilitate insulin signaling, improve insulin sensitivity, and reduce blood glucose concentration in conditions associated with insulin resistance, including type 2 diabetes, PCOS, and gestational diabetes.
• Phytate Metabolism: Myo-inositol can be released from dietary phytate by bacterial phytase activity in the colon. Phytate supplementation has been associated with increased propionate production in the stool and promotion of HDAC3 activity in the gut.

Technology Process of Inositol

There total 102 articles about Inositol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

(+/-)-1,2:4,5-di-O-isopropylidene-myo-inositol (51548-88-0,96039-15-5,98974-89-1,128110-25-8) → D-myo-inositol (87-89-8)

Guidance literature:

palladium dihydroxide; In methanol; for 88h; Heating;

DOI:10.1016/j.tet.2007.02.096

Reference yield: 96.0%

2,4,6-tri-O-benzyl-1,3,5-O-orthoformate-D-myo-inositol → D-myo-inositol (87-89-8)

Guidance literature:

palladium dihydroxide; In methanol; for 72h; Heating;

DOI:10.1016/j.tet.2007.02.096

Reference yield: 95.0%

(±)-2,3:5,6-di-O-isopropylidene-1,4-di-O-benzyl-myo-inositol → D-myo-inositol (87-89-8)

Guidance literature:

palladium dihydroxide; In methanol; for 22h; Heating;

DOI:10.1016/j.tet.2007.02.096

upstream raw materials:

inositol peracetate

benzenehexol

sequoyitol

(+)-Conduritol E epoxide

Downstream raw materials:

inositol hexanicotinate

furfural

tetrahydroxy-1,4-quinone

glucuronic acid

Refernces

• 1、 Bartow,Walker. "". . p. 300. Retrieved 1938.
• 2、 Puschmann, Robert,Harmel, Robert K.,Fiedler, Dorothea. "Analysis of metabolically labeled inositol phosphate messengers by NMR". . p. 35 - 52. Retrieved 2020/06/23.
• 3、 -. "Method for the production of inositol phytin". Paragraph 0021-0024. . Retrieved 2017/03/17.