Basic information
- CAS
700-06-1- Standard SMILES
OCc1c[nH]c2ccccc12- InChIKey
IVYPNXXAYMYVSP-UHFFFAOYSA-N- Molecular formula
- C9H9NO
- Average molar mass
- 147.17 g/mol
- Monoisotopic mass
- 147.06841391
Overview
Indole-3-methanol is an indolyl alcohol carrying a hydroxymethyl group at position 3. It is a constituent of the cruciferous vegetables and had anticancer activity. It has a role as an antineoplastic agent and a plant metabolite.
Names & identifiers
- Preferred name
- Indole-3-Carbinol
- IUPAC
- 1H-indol-3-ylmethanol
- English name
- Indole-3-carbinol
- Molecular formula
- C9H9NO
- Molecular weight
- 147.17
Names & synonyms
Indole-3-carbinol700-06-1INDOLE-3-METHANOL3-Hydroxymethylindole1H-Indole-3-methanol1H-indol-3-ylmethanol3-IndolylcarbinolI3C cpdDTXSID7031458Indole 3-carbinolNSC-525801C11E72455F
Show more names
I3CIndol-3-carbinolINDOLE-3-CARBINOLEThermal conductive oile-3-carbinoLndolemethanol
DTXCID5011458CHEBI:24814RefChem:148195211-836-23-Indolemethanol(1H-Indol-3-yl)methanolIndinol3-Indolylmethanol
Database identifiers
- CAS
700-06-1- PubChem CID
- 3712
- DTXSID
DTXSID7031458- ChEMBL
CHEMBL155625- ChEBI
CHEBI:24814- UNII
- C11E72455F
- EC Number
- 211-836-2
- Nikkaji
- J193.059A
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 36 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 138
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Solubility7 [ug/mL] (The mean of the results at pH 7.4)
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point90 °C
Physical DescriptionSolid
Collision Cross Section122.38 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 96 · 96-99 °C (lit.)
- Boiling point
- 267.28 °C · 267.28°C (rough estimate)
- Density
- 1.1135 · 1.1135 (rough estimate)
- refractive index
- 1.567 · 1.5670 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (97.8%): Causes skin irritation [Warning Skin corrosion/irritation]
P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Hazard Classes and CategoriesSkin Irrit. 2 (97.8%)
Toxicology
Carcinogen Classification
Indole-3-Carbinol
TR-584: Toxicology Studies of Indole-3-Carbinol (CASRN 700-06-1) in F344/N Rats and B6C3F1/N Mice and Toxicology and Carcinogenesis Studies of Indole-3-Carbinol in Harlan Sprague Dawley Rats and B6C3F1/N Mice (Gavage Studies) (2017 )
05/22/14
No Evidence
Some Evidence
Clear Evidence
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- NL9483000
- hs_code
- 29339900
- risk_code
- 36/38
- Signal word
- Warning
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationAgents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved.
Applications
OccurrenceIndole-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).
UsesIndole-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.
General DescriptionIndole-3-carbinol is a novel secondary plant metabolite produced in cruciferous vegetables, such as cabbage, cauliflower and brussels sprouts.
Preparation methods
PreparationUsing 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%.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
Related reactions
8 records
Compound notes
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