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700-06-1

Basic Information
CAS No.: 700-06-1
Name: Indole-3-carbinol
Article Data: 37
Cas Database
Molecular Structure:
Molecular Structure of 700-06-1 (Indole-3-carbinol)
Formula: C9H9NO
Molecular Weight: 147.177
Synonyms: Indole-3-methanol(6CI,7CI,8CI);3-(Hydroxymethyl)indole;3-Indolylcarbinol;3-Indolylmethanol;Indinol;NSC 525801;Indole-3-methanol;
EINECS: 211-836-2
Density: 1.272 g/cm3
Melting Point: 96-99 °C(lit.)
Boiling Point: 360.6 °C at 760 mmHg
Flash Point: 171.9 °C
Solubility: N/A
Appearance: Off-white powder
Hazard Symbols: IrritantXi
Risk Codes: 36/38
Safety: 26-36
Transport Information: N/A
PSA: 36.02000
LogP: 1.66020
Synthetic route
120-72-9

indole

50-00-0

formaldehyd

700-06-1

indole-3-carbinol

Conditions
ConditionsYield
With sodium methylate for 8h; Heating;100%
With methanol; sodium hydrogencarbonate
With sodium methylate
487-89-8

Indole-3-carboxaldehyde

700-06-1

indole-3-carbinol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0℃; for 1h;100%
With formic acid In ethanol at 80℃; for 12h; Catalytic behavior;91%
With ammonia; calcium In tetrahydrofuran at -33℃; for 2h; other reagents: lithium, sodium, liq. ammonia;80%
942-24-5

3-methoxycarbonylindole

700-06-1

indole-3-carbinol

Conditions
ConditionsYield
Stage #1: 3-methoxycarbonylindole With pentadec-3-en-2-one; trimethylsilyl trifluoromethanesulfonate; triphenylphosphine In dichloromethane at -78 - 0℃; for 1h; Inert atmosphere;
Stage #2: With diisobutylaluminium hydride In hexane; dichloromethane at -78℃; Inert atmosphere;
Stage #3: With potassium carbonate In methanol; hexane; dichloromethane at 20℃; for 0.5h; Inert atmosphere;
84%
487-89-8

Indole-3-carboxaldehyde

124-40-3

dimethyl amine

A

700-06-1

indole-3-carbinol

B

87-52-5

3-(Dimethylaminomethyl)indole

Conditions
ConditionsYield
With sodium tetrahydroborate; water In methanol at 55 - 60℃; for 2.5h;A 25%
B 74%
487-89-8

Indole-3-carboxaldehyde

A

700-06-1

indole-3-carbinol

B

22259-53-6

3-aminomethylindole

C

93742-14-4

bis(indol-3-ylmethyl)amine

Conditions
ConditionsYield
With ammonium hydroxide; sodium tetrahydroborate In methanol at 14 - 18℃; for 20h;A 72%
B 9%
C 13%
487-89-8

Indole-3-carboxaldehyde

A

700-06-1

indole-3-carbinol

B

N-((1H-indol-3-yl)methyl)formamide

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 20℃; for 1.5h; Leukardt-Wallach Amination;A 30%
B 49%
87-51-4

indole-3-acetic acid

A

83-34-1

3-Methylindole

B

487-89-8

Indole-3-carboxaldehyde

C

700-06-1

indole-3-carbinol

D

59027-01-9

3-(3-methylindol-1-yl)methylindole

Conditions
ConditionsYield
With 1,3,6,8-tetra-n-butylpyrimido<5,4-g>pteridine-2,4,5,7(1H,3H,6H,8H)-tetrone 10-oxide In acetonitrile for 0.0833333h; Irradiation;A 14%
B 36%
C 12%
D 8%
With 1,3,6,8-tetra-n-butylpyrimido<5,4-g>pteridine-2,4,5,7(1H,3H,6H,8H)-tetrone 10-oxide In acetonitrile for 0.166667h; Product distribution; Ambient temperature; Irradiation; depends on time and wavelength of irradiation and ratio of reacted compounds;
110-88-3

1,3,5-Trioxan

120-72-9

indole

67-56-1

methanol

124-41-4

sodium methylate

700-06-1

indole-3-carbinol

17206-03-0

1-(1H-indol-3-yl)-N,N-dimethylmethanamine oxide

700-06-1

indole-3-carbinol

Conditions
ConditionsYield
With sodium hydroxide; diethyl ether; water
5457-31-8

(3-indolylmethyl)trimethylammonium iodide

700-06-1

indole-3-carbinol

Conditions
ConditionsYield
With sodium hydroxide; diethyl ether; water
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  • Indole-3-carbinol   	  CAS: 700-06-1

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    Indole-3-carbinol CAS: 700-06-1

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    Name Indole-3-carbinol Synonyms 3-Hydroxymethylindole; 3-Indolemethanol; Indole-3-methanol CAS NO. 700-06-1 Molecular Formula C9H9NO

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    Indole-3-carbinol 700-06-1 Indole-3-carbinol Basic information Product Name: Indole-3-carbinol Synonyms: 3-indolylcarbinol;I3C;INDOLE-3-METHANOL;INDOLE-3-CARBINOL;INDOLE-3-CARBINOLE;AK

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Chemistry

Molecular Structure of Indole-3-methanol (CAS NO.700-06-1):

Molecular Formula: C9H9NO
Molecular Weight: 147.1739
IUPAC Name: 1H-Indol-3-ylmethanol
CAS NO: 700-06-1
Appearance:white to off white crystals
Melting point: 96-99 °C
Index of Refraction: 1.705
Molar Refractivity: 44.97 cm3
Molar Volume: 115.6 cm3
Surface Tension: 61.7 dyne/cm
Density: 1.272 g/cm3
Flash Point: 171.9 °C
Enthalpy of Vaporization: 63.98 kJ/mol
Boiling Point: 360.6 °C at 760 mmHg
Vapour Pressure: 7.89E-06 mmHg at 25°C
Classification Code: Anticarcinogenic agents; Antineoplastic Agents; Protective Agents; Reproductive Effect
Synonyms: 3-Hydroxymethylindole ; 3-Indolylcarbinol ; 5-21-03-00045 (Beilstein Handbook Reference) ; AI3-60090 ; BRN 0121323 ; CCRIS 3261 ; EINECS 211-836-2 ; Indinol ; Indole 3 carbinol ; Indole-3-carbinol ; NSC 525801 ; 1H-Indole-3-methanol (9CI)  
SMILES: OCc2c1ccccc1nc2
InChI: InChI=1/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2
InChIKey: IVYPNXXAYMYVSP-UHFFFAOYAO
Std. InChI: InChI=1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2
Std. InChIKey: IVYPNXXAYMYVSP-UHFFFAOYSA-N

Uses

  Indole-3-methanol (CAS NO.700-06-1) can prevent the development of estrogen-enhanced cancers including breast, endometrial and cervical cancers. It has be shown to inhibit carcinogenesis in several animal species, but it enhances tumor incidence if administered at a post-initiation stage.

Production

  Indole-3-methanol (CAS NO.700-06-1) naturally exists in vegetables such as cabbage, broccoli, brussels sprouts, and kale. It is also widely available in supplement form. In 1985,B Sundberg and his Co-worker did a study about "Identification and Quantification of Indole-3-methanol in Etiolated Seedlings of Scots Pine"(Pinus sylvestris L.). Indole-3-methanol did exist in buffer extract from etiolated seedlings of Pinus sylvestris L.And the stability of indole-3-methanol at different pH levels was investigated.

  As a metabolism of indole-3-acetic acid, Indole-3-methanol can be produced by the oxidation of indole-3-acetic acid catalyzed by two cytosolic basic isoperoxidases from Lupinus. This study has been done by A. Barceló in 1990. While indole-3-methanol is only a minor product of the oxidation of indole-3-acetic acid catalyzed by extracellular acidic isoperoxidases, it is the only product of the oxidation of indole-3-acetic acid catalyzed by two cytosolic basic isoperoxidases (EC 1.11.1.7) from lupin (Lupinus albus L.) hypocotyls. It can be produced by the breakdown of the glucosinolate glucobrassicin.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LDLo subcutaneous 500mg/kg (500mg/kg) BEHAVIORAL: COMA Food and Cosmetics Toxicology. Vol. 18, Pg. 159, 1980.

Safety Profile

Safty informations about Indole-3-methanol (CAS NO.700-06-1):
Hazard Codes:XiIrritant
Risk Statements:36/38
36/38 (Irritating to the eyes and skin)
Safety Statements:26-36
26 (In case of contact with eyes,rinse immediately with plenty of water and seek medical advice)
36 (Wear suitable protective clothing)
WGK Germany:3
RTECS:NL9483000
Hazard Note:Irritant
Moderately toxic by subcutaneous route. An experimental teratogen. When heated to decomposition it emits toxic fumes of NOx.

Specification

Handling and Storage
Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. 
Storage: Store in a tightly closed container. Store in a dry area. Keep refrigerated. (Store below 4oC/39oF.)