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:

99% ^*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:

hexa-O-formyl-myo-inositol

inositol peracetate

(+/-)-2,5-dibromo-1,3,4,6-tetra-O-acetyl-2,5-dideoxy-asymm.-inositol

(+/-)-1,5-dibromo-2,3,4,6-tetra-O-acetyl-1,5-dideoxy-asymm.-inositol

Refernces

Complete and remarkable reversal of chemoselectivity in [4 + 2] cycloadditions involving electron-poor indoles as dienophiles. Diels-Alder versus hetero-Diels-Alder processes

10.1021/jo034719b

The research explores the chemoselectivity of electron-poor indoles in [4 + 2] cycloadditions, focusing on the competition between Diels-Alder (DA) and hetero-Diels-Alder (HDA) reactions. The study aims to demonstrate the influence of electronic and structural parameters on the reactivity of indoles, leading to either DA or HDA products. The researchers used various indole derivatives, such as indole-3-carboxaldehyde, indole-3-glyoxalate, and N-substituted indole-3-glyoxamides, along with dienes like 2,3-dimethylbutadiene and Danishefsky diene. The reactions were activated thermally, under high pressure, or with the aid of Lewis acids like zinc chloride and europium tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionate) (EuFOD). The conclusions highlight the ability to modulate the reactivity of the indole dienophile to favor either the classical DA process or the HDA reaction, with the products strongly depending on the type of electron-withdrawing substituent on the indole, the diene used, and the activation method. The study also reveals a remarkable reversal of chemoselectivity based on the number and nature of substituents on the acyclic nitrogen atom of the indole-3-glyoxamides.

News on inositol liquid crystals

10.1080/10587259408037774

The research focuses on the synthesis and characterization of various derivatives of inositols, which are stereoisomers of 1,2,3,4,5,6-hexahydroxycyclohexane. The purpose of the study was to investigate how the number, position, and stereochemical arrangement of hydroxyl groups and alkoxy chains on the cyclohexane ring affect the occurrence, type, and stability of thermotropic mesophases in these compounds. The research concluded that the presence of unsaturated six-membered ring units, such as quinoic or aromatic groups, negatively impacts the exhibition of mesophases, and that axial hydroxy and alkoxy groups tend to destabilize the smectic A or hexagonal columnar phase. The study also identified two ways to transform a hexagonal columnar phase into a smectic A phase. The chemicals used in this process included a variety of alkylating agents, inositol derivatives, and solvents such as toluene, benzene, and ethyl acetate, among others, to synthesize and characterize the inositol liquid crystals.

Preparation of L-α-phosphatidyl-D-myo-inositol 3-phosphate (3-PIP) and 3,5-biphosphate (3,5-PIP₂)

10.1016/S0960-894X(00)00315-2

The research focuses on the practical and asymmetric total synthesis of two important phospholipids, L-α-phosphatidyl-D-myo-inositol 3-phosphate (3-PIP) and 3,5-bisphosphate (3,5-PIP2). These compounds play crucial roles in membrane trafficking and intracellular signaling in eukaryotic cells. The purpose of the study was to develop efficient synthetic routes for these metabolites to facilitate further investigation into their physiological significance and biochemical interconversions. The researchers utilized a readily available myo-inositol derivative and short-chain, cross-linkable aminoether analogues as starting materials.