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87-89-8

Basic Information
CAS No.: 87-89-8
Name: Inositol
Molecular Structure:
Molecular Structure of 87-89-8 (Inositol)
Formula: C6H12O6
Molecular Weight: 180.16
Synonyms: INOSITE; (1R,2r,3S,4R,5s,6S)-cyclohexane-1,2,3,4,5,6-hexaol; nositol; myo-Inositol; cis-1,2,3,5-trans-4,6-Cyclohexanehexol; meso-inositol; Inosital; bios I; INS; Nucite; 2-(PROPYLAMINO)-M-PROPIONOTOLUIDIDE HYDROCHLORIDE; Dambose; Mesol; Mesovit; 查看更多英文别名 收起
EINECS: 201-781-2
Density: 2.039 g/cm3
Melting Point: 222-227 °C(lit.)
Boiling Point: 291.326 °C at 760 mmHg
Flash Point: 143.387 °C
Solubility: 4 g/100 mL (25 °C) in water
Appearance: white powder
Hazard Symbols:
Risk Codes:
Safety: 22-24/25
Transport Information:
PSA: 121.38000
LogP: -3.83460
Synthetic route
51548-88-0, 96039-15-5, 98974-89-1, 128110-25-8

(+/-)-1,2:4,5-di-O-isopropylidene-myo-inositol

87-89-8

D-myo-inositol

Conditions
ConditionsYield
palladium dihydroxide In methanol for 88h; Heating;97%

2,4,6-tri-O-benzyl-1,3,5-O-orthoformate-D-myo-inositol

87-89-8

D-myo-inositol

Conditions
ConditionsYield
palladium dihydroxide In methanol for 72h; Heating;96%
With Pd(OH)2/C In methanol for 72h; Reflux;

(±)-2,3:5,6-di-O-isopropylidene-1,4-di-O-benzyl-myo-inositol

87-89-8

D-myo-inositol

Conditions
ConditionsYield
palladium dihydroxide In methanol for 22h; Heating;95%

1D-1-O-Acetyl-myo-inositol

87-89-8

D-myo-inositol

Conditions
ConditionsYield
With sodium methylate In methanol at 70℃; for 3h; Deacetylation;94%

2-O-tert-butyldimethyl-myo-inositol 4,6-carbonate 1,3,5-orthoformate

A

87-89-8

D-myo-inositol

B

myo-inositol 4,6-carbonate

Conditions
ConditionsYield
With water; trifluoroacetic acid at 65 - 70℃;A n/a
B 83%

2-O-(tert-butyldimethylsilyl)-4,6-O-methylene-myo-inositol 1,3,5-orthoformate

A

87-89-8

D-myo-inositol

B

1259936-03-2

4,6-O-methylene-myo-inositol

Conditions
ConditionsYield
With methanol; toluene-4-sulfonic acid In chloroform at 40℃; for 48h;A n/a
B 74%
15421-51-9

myo-inositol 1-phosphate

87-89-8

D-myo-inositol

Conditions
ConditionsYield
With alkaline phosphatase type III from Escherichia coli In various solvent(s) at 25℃; for 16h; pH=8.0; Substitution;63.6%
1254-38-2

inositol peracetate

87-89-8

D-myo-inositol

Conditions
ConditionsYield
With hydrogenchloride
With sodium methylate In methanol for 2h;
608-80-0

benzenehexol

87-89-8

D-myo-inositol

Conditions
ConditionsYield
With water; hydrogen; palladium at 50 - 55℃;
With ethanol; nickel at 125℃; under 95616 Torr; Hydrogenation;
With water; palladium at 20℃; Hydrogenation.sowie bei 55grad;
523-92-2

sequoyitol

87-89-8

D-myo-inositol

Conditions
ConditionsYield
With hydrogen iodide
With hydrogen iodide Heating;0.08 g
145107-29-5

(+)-Conduritol E epoxide

A

87-89-8

D-myo-inositol

B

643-10-7

allo-inositol

Conditions
ConditionsYield
With barium dihydroxide
Conditions
ConditionsYield
In water for 48h; Product distribution; biosynthesis with Simmondsia chinensis, various time;
22350-68-1

(1R)-1-L-O-methyl-myo-inositol

87-89-8

D-myo-inositol

Conditions
ConditionsYield
With hydrogen iodide In water for 1h; Heating;0.1 g
With water Reflux;
93712-94-8

D-Myo-inositol-1-monophosphate

87-89-8

D-myo-inositol

Conditions
ConditionsYield
In water at 40℃; rice bran acid phosphatase, 0.2 M acetate buffer;
93712-94-8

Myo-inositol-2-monophosphate

87-89-8

D-myo-inositol

Conditions
ConditionsYield
In water at 40℃; rice bran acid phosphatase, 0.2 M acetate buffer;
93712-94-8

L-Myo-inositol-3-monophosphate

87-89-8

D-myo-inositol

Conditions
ConditionsYield
In water at 40℃; rice bran acid phosphatase, 0.2 M acetate buffer;
50474-02-7

1,2:4,5-Dianhydro-cis-inosit

A

87-89-8

D-myo-inositol

B

488-55-1

muco-inositol

Conditions
ConditionsYield
With sulfuric acid for 3h; Heating;A 14 % Spectr.
B 86 % Spectr.

A

87-89-8

D-myo-inositol

B

488-55-1

muco-inositol

C

488-59-5

myo-inositol

18685-70-6

chiro-inositol

Conditions
ConditionsYield
With sulfuric acid for 3h; Heating;A 0.5 % Spectr.
B 80 % Spectr.
C 0.5 % Spectr.
D 19 % Spectr.
139013-60-8

(1S,2R,3R,4R)-3,4-O-Isopropylidenecyclohex-5-ene-1,2,3,4-tetraol

A

87-89-8

D-myo-inositol

B

488-55-1

muco-inositol

Conditions
ConditionsYield
With sulfuric acid; 3-chloro-benzenecarboperoxoic acid 1.) CH2Cl2; Yield given. Multistep reaction. Yields of byproduct given;
2831-74-5

D-myo-inositol-3-phosphate

87-89-8

D-myo-inositol

Conditions
ConditionsYield
With pAD1.88A; phosphatse from Escherichia coli JWF1
145107-29-5

(+)-Conduritol E epoxide

aqueous barium hydroxide

aqueous barium hydroxide

A

87-89-8

D-myo-inositol

B

643-10-7

allo-inositol

Conditions
ConditionsYield
at 100℃;
2.3.5.6-tetrahydroxy-benzoquinone-(1.4)

2.3.5.6-tetrahydroxy-benzoquinone-(1.4)

87-89-8

D-myo-inositol

Conditions
ConditionsYield
With water; palladium at 20℃; Hydrogenation;
With palladium on activated charcoal; water at 20℃; Hydrogenation;
levorotatory mesoinositol-tetraphosphoric acid

levorotatory mesoinositol-tetraphosphoric acid

87-89-8

D-myo-inositol

Conditions
ConditionsYield
With water at 130℃;
With sulfuric acid at 130℃;
phytic acid

phytic acid

87-89-8

D-myo-inositol

Conditions
ConditionsYield
With phytase
phytin

phytin

87-89-8

D-myo-inositol

Conditions
ConditionsYield
With mineral acid
With phytase
With water
With phytase
With sulfuric acid Hydrolysis;
488-64-2

myo-2-inosose

platinum

platinum

87-89-8

D-myo-inositol

Conditions
ConditionsYield
Hydrogenation;
salt of/the/ phytic acid

salt of/the/ phytic acid

87-89-8

D-myo-inositol

tethelin

tethelin

87-89-8

D-myo-inositol

Conditions
ConditionsYield
Hydrolysis;
87-89-8

D-myo-inositol

98-80-6

phenylboronic acid

69814-44-4

rac-1:2,3:5,4:6-O1:O2,O3:O5,O4:O6-tris(phenylboronato)-myo-inositol

Conditions
ConditionsYield
at 95℃; for 1h;100%
87-89-8

D-myo-inositol

108-94-1

cyclohexanone

6763-47-9

rac-1,2-O-cyclohexylidene-myo-inositol

Conditions
ConditionsYield
Stage #1: D-myo-inositol; cyclohexanone With toluene-4-sulfonic acid In N,N-dimethyl-formamide; toluene at 122 - 136℃; for 10h; Condensation;
Stage #2: With ethanol; toluene-4-sulfonic acid at 20℃; for 48h; alcoholysis;
98%
With toluene-4-sulfonic acid97%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; toluene for 9h; Heating;93%
87-89-8

D-myo-inositol

77-76-9

2,2-dimethoxy-propane

128387-20-2

L-1,2-O-isopropylidene-myo-inositol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dimethyl sulfoxide98%
87-89-8

D-myo-inositol

108-24-7

acetic anhydride

1254-38-2

inositol peracetate

Conditions
ConditionsYield
With copper(II) perchlorate hexahydrate In neat (no solvent) at 20℃; for 0.166667h; Inert atmosphere;95%
iron(III) chloride at 28 - 32℃; for 0.166667h;86%
With zinc(II) chloride
87-89-8

D-myo-inositol

112-13-0

n-decanoyl chloride

Hexa-O-decanoyl-myo-inosit

Conditions
ConditionsYield
With trifluoroacetic acid for 15h; Ambient temperature;95%
87-89-8

D-myo-inositol

98-88-4

benzoyl chloride

78-39-7

Triethyl orthoacetate

2,4,6-tri-O-benzoyl-myo-inosityl 1,3,5-orthoacetate

Conditions
ConditionsYield
Stage #1: D-myo-inositol; Triethyl orthoacetate With toluene-4-sulfonic acid In N,N-dimethyl-formamide for 8h; Heating;
Stage #2: benzoyl chloride In pyridine at 20℃;
95%
87-89-8

D-myo-inositol

98-88-4

benzoyl chloride

162062-52-4

1,3-di-O-benzoyl-myo-inositol

Conditions
ConditionsYield
With triethylamine; lithium chloride In N,N-dimethyl acetamide at -10℃; for 4h; regioselective reaction;95%
Stage #1: D-myo-inositol; benzoyl chloride With triethylamine; lithium chloride In N,N-dimethyl acetamide at -10℃; for 4h;
Stage #2: With pyridine; chloro-trimethyl-silane In N,N-dimethyl acetamide at 0℃; for 5h;
Stage #3: With trifluoroacetic acid In methanol; chloroform at 20℃; for 4h;
95%
87-89-8

D-myo-inositol

123-62-6

propionic acid anhydride

5776-50-1

Hexakispropionylmyoinositol

Conditions
ConditionsYield
With Cl(1-)*C5H14NO(1+)*3ZnCl2 In neat (no solvent) at 20℃; for 2h; Green chemistry;95%
1445-45-0

Trimethyl orthoacetate

87-89-8

D-myo-inositol

106-95-6

allyl bromide

C18H30O9

Conditions
ConditionsYield
Stage #1: Trimethyl orthoacetate; D-myo-inositol With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 100℃; for 2h;
Stage #2: allyl bromide With sodium hydride In N,N-dimethyl-formamide at 20℃; for 3h; Further stages;
95%
87-89-8

D-myo-inositol

98-88-4

benzoyl chloride

122-51-0

orthoformic acid triethyl ester

(1R,3s,5r,6R,7S,8s,9S)-2,4,10-trioxaadamantane-6,8,9-triyl tribenzoate

Conditions
ConditionsYield
Stage #1: D-myo-inositol; orthoformic acid triethyl ester With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 100℃;
Stage #2: benzoyl chloride In pyridine at 20℃;
94%
87-89-8

D-myo-inositol

707-07-3

orthobenzoic acid trimethyl ester

C13H14O6

Conditions
ConditionsYield
With camphor-10-sulfonic acid In dimethyl sulfoxide Inert atmosphere;94%
With toluene-4-sulfonic acid In dimethyl sulfoxide at 100℃; for 5h; Inert atmosphere;
87-89-8

D-myo-inositol

67-68-5

dimethyl sulfoxide

C11H16O8

Conditions
ConditionsYield
With trichlorophosphate at 65℃; for 0.5h;92%
87-89-8

D-myo-inositol

97419-16-4

1,1,1-Trimethoxy-2,2-dimethyl-propane

3-tert-Butyl-2,4,10-trioxa-tricyclo[3.3.1.13,7]decane-6,8,9-triol

Conditions
ConditionsYield
With camphor-10-sulfonic acid In dimethyl sulfoxide at 60℃; for 15h;91%
87-89-8

D-myo-inositol

149-73-5

trimethyl orthoformate

myo-inosytol 1,3,5-orthoformate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide Inert atmosphere;91%
toluene-4-sulfonic acid In DMF (N,N-dimethyl-formamide) at 120℃; for 7h;
1445-45-0

Trimethyl orthoacetate

87-89-8

D-myo-inositol

myo-inositol 1,3,5-orthoacetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 90 - 100℃;91%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 100℃; for 10h;10%
87-89-8

D-myo-inositol

122-51-0

orthoformic acid triethyl ester

98510-20-4

myo-Inositol orthoformate

Conditions
ConditionsYield
With Amberlyst 15 In N,N-dimethyl-formamide at 100℃; for 3h;90%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide89%
With o-toluenesulfonic acid In N,N-dimethyl-formamide at 100℃; for 16h;84%
87-89-8

D-myo-inositol

79-30-1

isobutyryl chloride

32077-77-3

Hexakisisobutyrylmyoinositol

Conditions
ConditionsYield
With pyridine; dmap at 80 - 85℃; for 1h;90%
87-89-8

D-myo-inositol

707-07-3

orthobenzoic acid trimethyl ester

myo-inositol 1,3,5-orthobenzoate

Conditions
ConditionsYield
With camphor-10-sulfonic acid In dimethyl sulfoxide at 80℃; under 22.5023 - 30.003 Torr; for 3h;90%
With camphor-10-sulfonic acid In dimethyl sulfoxide at 80℃; for 5h;84%
With H2SO4 supported on silica In dimethyl sulfoxide at 60℃; under 300.03 Torr; for 0.5h; Inert atmosphere; Green chemistry;83%
87-89-8

D-myo-inositol

108-24-7

acetic anhydride

1431370-12-5

1,3-di-O-acetyl-myo-inositol

Conditions
ConditionsYield
With dibutyltin diacetate; triethylamine; lithium chloride In N,N-dimethyl acetamide at -10℃; for 2h;90%
1189-71-5

isocyanate de chlorosulfonyle

87-89-8

D-myo-inositol

myo-inositol hexacarbamate

Conditions
ConditionsYield
In acetonitrile at 20℃; for 1.5h; Cooling with ice;90%
87-89-8

D-myo-inositol

122-51-0

orthoformic acid triethyl ester

myo-inositol-1,3,5-O-orthoformate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 100℃; for 24h;89%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 140℃; for 3h;87%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 110℃; for 28h; Inert atmosphere;83%
87-89-8

D-myo-inositol

149-73-5

trimethyl orthoformate

98510-20-4

myo-Inositol orthoformate

Conditions
ConditionsYield
With TSA In N,N-dimethyl-formamide at 110℃; for 5h;89%
In N,N-dimethyl-formamide70%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 99.9℃; for 3h;
87-89-8

D-myo-inositol

58479-61-1

tert-butylchlorodiphenylsilane

1196789-46-4

1,3-di-O-tert-butyldiphenylsilyl-myo-inositol

Conditions
ConditionsYield
With pyridine In dimethyl sulfoxide at 20℃; for 72h; regioselective reaction;89%
With pyridine In dimethyl sulfoxide at 20℃; for 72h;89%
87-89-8

D-myo-inositol

69304-37-6

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

123270-13-3

1,6:3,4-bis-O-(tetraisopropyldisiloxane-1,3-diyl)-myo-inositol

Conditions
ConditionsYield
With pyridine In dimethyl sulfoxide at 20℃; for 20h; regioselective reaction;88%
With pyridine In dimethyl sulfoxide at 20℃; for 20h;88%
With pyridine Ambient temperature;66%
87-89-8

D-myo-inositol

3282-30-2

pivaloyl chloride

1196789-44-2

1,3-di-O-pivaloyl-myo-inositol

Conditions
ConditionsYield
With triethylamine; lithium chloride In N,N-dimethyl acetamide at 0℃; for 10h; regioselective reaction;88%
With triethylamine; lithium chloride In N,N-dimethyl acetamide at 0℃; for 10h;88%
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Specification

Inositol(CAS NO.87-89-8) is also named as 1,2,3,5-trans-4,6-Cyclohexanehexol, cis-; AI3-16111; CCRIS 6745; Dambose; Inosital; Inositene; Inositina; Inositol (VAN). It is white powder. Inositol or cyclohexane-1,2,3,4,5,6-hexol is a chemical compound with formula C6H12O6 or (-CHOH-)6, a sixfold alcohol (polyol) of cyclohexane. It is almost tasteless, with a small amount of sweetness. It is soluble in water, slightly soluble in ethanol, acetic acid, ethylene glycol and glycerin, insoluble in ether, acetone and chloroform.

Physical properties about Inositol are: (1)ACD/LogP: -3.861; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -3.86; (4)ACD/LogD (pH 7.4): -3.86; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 6; (10)#H bond donors: 6; (11)#Freely Rotating Bonds: 6; (12)Index of Refraction: 1.784; (13)Molar Refractivity: 37.213 cm3; (14)Molar Volume: 88.375 cm3; (15)Polarizability: 14.752 10-24cm3; (16)Surface Tension: 101.601997375488 dyne/cm; (17)Density: 2.039 g/cm3; (18)Flash Point: 143.387 °C; (19)Enthalpy of Vaporization: 61.583 kJ/mol; (20)Boiling Point: 291.326 °C at 760 mmHg

Preparation of Inositol:  Inositol is produced from glucose-6-phosphate (G-6-P) in two steps. First, G-6-P is isomerised by ISYNA1 to inositol 1-phosphate; then it is dephosphorylated by IMPase 1 to give free Inositol . In humans most inositol is synthesized in the kidneys, in typical amounts of a few grams per day.
 
Uses of Inositol: Inositol has been used as an adulterant (or cutting agent) in many illegal drugs, such as cocaine, methamphetamine, and sometimes heroin.[citation needed] It is presumed that this use is connected with one or more of the substance's properties of solubility, powdery texture, or reduced sweetness (50%) as compared with more common sugars. Inositol is also used as a stand-in for cocaine on television.

You can still convert the following datas into molecular structure:
(1)InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4+,5-,6-; S27:Take off immediately all contaminated clothing.
(2)InChIKey=CDAISMWEOUEBRE-GPIVLXJGSA-N;
(3)Smiles[C@@H]1([C@@H]([C@H]([C@@H]([C@H]([C@H]1O)O)O)O)O)O

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 10gm/kg (10000mg/kg)   Toksikologicheskii Vestnik. Vol. (2), Pg. 25, 1994.
rat LD50 intraperitoneal > 3gm/kg (3000mg/kg)   Japanese Kokai Tokyo Koho Patents. Vol. #92-9328,
rat LD50 intravenous > 750mg/kg (750mg/kg)   Japanese Kokai Tokyo Koho Patents. Vol. #92-9328,