ChemicalBook > CAS DataBase List > Indole-3-carbinol

Indole-3-carbinol

Product Name
Indole-3-carbinol
CAS No.
700-06-1
Chemical Name
Indole-3-carbinol
Synonyms
I3C;Indol-3-carbinol;3-INDOLEMETHANOL;INDOLE-3-METHANOL;3-indolylcarbinol;INDOLE-3-CARBINOLE;Indinol;e-3-carbinoL;ndolemethanol;AKOS NCG1-0099
CBNumber
CB7295605
Molecular Formula
C9H9NO
Formula Weight
147.17
MOL File
700-06-1.mol
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Indole-3-carbinol Property

Melting point:
96-99 °C (lit.)
Boiling point:
267.28°C (rough estimate)
Density 
1.1135 (rough estimate)
refractive index 
1.5670 (estimate)
storage temp. 
2-8°C
solubility 
soluble in Methanol
form 
Crystalline Powder or Flakes
pka
15.10±0.10(Predicted)
color 
Off-white to yellow-orange
BRN 
121323
Stability:
2-80C
InChI
InChI=1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2
InChIKey
IVYPNXXAYMYVSP-UHFFFAOYSA-N
SMILES
N1C2=C(C=CC=C2)C(CO)=C1
LogP
1.366 (est)
CAS DataBase Reference
700-06-1(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/38
Safety Statements 
26-36
WGK Germany 
3
RTECS 
NL9483000
Hazard Note 
Irritant
HS Code 
29339900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
I7256
Product name
Indole-3-carbinol
Packaging
1g
Price
$68.2
Updated
2024/03/01
Sigma-Aldrich
Product number
I7256
Product name
Indole-3-carbinol
Packaging
5g
Price
$93.4
Updated
2024/03/01
TCI Chemical
Product number
I0496
Product name
3-Indolemethanol
Purity
>98.0%(HPLC)(N)
Packaging
5g
Price
$40
Updated
2024/03/01
TCI Chemical
Product number
I0496
Product name
3-Indolemethanol
Purity
>98.0%(HPLC)(N)
Packaging
25g
Price
$195
Updated
2024/03/01
Alfa Aesar
Product number
L15762
Product name
3-Indolemethanol, 97%
Packaging
1g
Price
$22.65
Updated
2024/03/01
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Indole-3-carbinol Chemical Properties,Usage,Production

Chemical Properties

Indole-3-carbinol is an off-white powder. It is soluble in organic solvents such as benzene, ethanol, DMSO, and dimethyl formamide (DMF), which should be purged with an inert gas. The solubility of Indole-3-carbinol in ethanol and DMF is approximately 10 mg/ml and approximately 3 mg/ml in DMSO. Indole-3-carbinol is an unstable compound that undergoes rapid oligomerization in acid pH environments, like the stomach.

Occurrence

Indole-3-carbinol is produced by members of the family Cruciferae, and particularly members of the genus Brassica (e.g., cabbage, radishes, cauliflower, broccoli, Brussels sprouts, and daikon).

Uses

Indole-3-carbinol has been used for encapsulation with poly-lactic-co-glycolic acid (PLGA), to study its in-vitro anti-cancerogenic effects on breast adenocarcinoma epithelial (MCF7), colon adenocarcinoma epithelial (Caco2), prostate carcinoma epithelial (PC3) cells. It has also been used as a cytochrome P4501A (CYP1A) inducer.

Definition

ChEBI: Indole-3-carbinol is an indolyl alcohol carrying a hydroxymethyl group at position 3. It is a constituent of the cruciferous vegetables and had anticancer activity.

Preparation

Using indole, phosphorus oxychloride and N,N-dimethylformamide as raw materials, indole-3-carbaldehyde was synthesized by Vilsmeier-Haack reaction with a yield of 87.1%.

Application

Indole-3-carbinol (I3C) is a secondary plant metabolite of 3-methylindole produced in Brassica family vegetables. It is an inhibitor of Amyloid-beta deposition and Inhibits cancinogenesis at the initiation stage. Indole-3-carbinol is used in cancer prevention, specifically for breast, cervical and colon cancers. It has also been widely used to address lupus.

Synthesis Reference(s)

Canadian Journal of Chemistry, 31, p. 775, 1953 DOI: 10.1139/v53-106
The Journal of Organic Chemistry, 61, p. 1493, 1996 DOI: 10.1021/jo951219c

General Description

Indole-3-carbinol is a novel secondary plant metabolite produced in cruciferous vegetables, such as cabbage, cauliflower and brussels sprouts.

Biochem/physiol Actions

Inhibits cancinogenesis at the initiation stage. Has be shown to inhibit carcinogenesis in several animal species, but it enhances tumor incidence if administered at a post-initiation stage. Found in cruciferous vegetables.

Anticancer Research

I3C is a bioactive compound majorly found in Brassica vegetables including broccoli,cauliflower, and collard greens. I3C and its derivative diindolylmethane (DIM)have been investigated for cancer prevention and treatment of breast, prostate, andovarian cancers. I3C partially modulates the tyrosine kinase/PI3K/Akt signalingpathway which leads to the prevention of lung adenocarcinoma which is induced byusing tobacco carcinogen in A/J mice. DIM transduces signaling via aryl hydrocarbon(Ah) receptor, NF-κB/Wnt/Akt/mTOR signaling pathways, cell cycle arrest,modulated cytochrome P450 enzymes, and altered angiogenetic and invasive,metastatic, and epigenetic behavior of cancer cells. Combination of DIM and I3Cinduces Nrf2-mediated phase II drug metabolizing genes (GSTm2, UGT1A1, andNQO1) and antioxidant genes (HO-1, SOD-1) (Weng et al. 2008; 2012).

Indole-3-carbinol Preparation Products And Raw materials

Raw materials

2,3-DICHLORO-5,8-DIHYDROXY-1,4-NAPHTHOQUINONE

Preparation Products

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View Lastest Price from Indole-3-carbinol manufacturers

Jinan Finer Chemical Co., Ltd
Product
Indole-3-carbinol 700-06-1
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
99%
Supply Ability
200mt
Release date
2021-11-12
Hebei Weibang Biotechnology Co., Ltd
Product
Indole-3-carbinol 700-06-1
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-20
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Indole-3-Carbinol 700-06-1
Price
US $75.00-25.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-28

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