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Product Name: Indole-3-carbinol
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DC Chemicals Limited
China
Product Name: Indole-3-carbinol
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Dayang Chem (Hangzhou) Co., Ltd.
China
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Zhejiang Hangyu API Co., Ltd
China
Product Name: Indole-3-carbinol
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Henan Tianfu Chemical Co., Ltd.
China
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700-06-1

700-06-1 structure

700-06-1 structure

Name: Indole-3-carbinol
Chemical Name: indole-3-methanol
CAS Number: 700-06-1
Molecular Formula: C₉H₉NO
Molecular Weight: 147.174
Catalog: Signaling Pathways Immunology/Inflammation Aryl Hydrocarbon Receptor
Create Date: 2018-07-13 17:48:14
Modify Date: 2024-01-02 14:30:45
Indole-3-carbinol suppresses NF-κB activity and also is an Aryl hydrocarbon receptor (AhR) agonist.

Name	indole-3-methanol
Synonyms	Indole-3-carbidol MFCD02683932 3-INDOLAMETHANOL 3-indolemethanol 1H-Indole-3-methanol (9CI) Indole-3-carbinol EINECS 211-836-2 3-IndoleCarbinol 1H-Indol-3-ylmethanol 1H-Indole-3-methanol (1H-indol-3-yl)-methanol (1H-indole-3-yl)-methanol indole-3-methanol I3C 3-hydroxymethyl-1H-indole 3-INDOLYLMETHANOL 3-indolylcarbinol

Description	Indole-3-carbinol suppresses NF-κB activity and also is an Aryl hydrocarbon receptor (AhR) agonist.
Related Catalog	Signaling Pathways >> Immunology/Inflammation >> Aryl Hydrocarbon Receptor Natural Products >> Alkaloid Research Areas >> Cancer
Target	NF-κB AhR
In Vitro	It is found that Indole-3-carbinol (I3C) inhibits the proliferation of THP-1 cells in a dose- and time dependent manner with minimal toxicity over normal monocytes. The AhR target genes (CYP1A1, IL1β) are overexpressed upon Indole-3-carbinol treatment (p<0.05 to p<0.001). The antiproliferative effects of Indole-3-carbinol are in association with programing cell death. Indole-3-carbinol downregulates BCL2 and upregulates FasR in THP-1 cells (p<0.05 to p<0.001). G1 cell cycle arrest is also observed using flow cytometry. G1-acting cell cycle genes (P21, P27 and P53) are overexpressed (p<0.05 to p<0.001), while CDK2 is downregulated upon Indole-3-carbinol treatment (p<0.01 to p<0.001)[1].Indole-3-carbinol suppresses NF-κB activity and stimulates the p53 pathway in pre-B acute lymphoblastic leukemia cells[2].
Cell Assay	THP-1 cells are cultured in RPMI 1640 supplemented with 10% FBS, 100 U/mL penicillin, 100 mg/mL streptomycin and 2 mM Glutamax in a fully humidified atmosphere with 5% CO2. Cells (2-5×105 mL-1) are seeded in six well plates followed by resuspension in complete growth media. THP-1 monocyte cells are then treated with 10 ng/mL phorbol 12-myristate 13-acetate as a tumor promoter to induce stable differentiation into attaching macrophage-like cells and overexpression of AhR. The cells are then treated with varying concentrations of Indole-3-carbinol (1, 10 and 100 μM, and 1 mM). THP-1 cells and enriching normal monocytes are seeded at 5×104 cells/well in 24-well plate with different concentrations of Indole-3-carbinol and observed for 24 and 48 h followed by MTT assay. The cells are incubated in triplicates in a final volume of 200 mL of Phenol Red free RPMI 1640 for 20 h . An aliquot of 20 mL of MTT solution (5 mg/mL) is added to each well and incubated for 4 h. Formazan crystals are formed. An amount of 300 mL DMSO is then added to each well as a cell lysis solution. Percentage of cell viability is assessed by spectrophotometry at 570 nm[1].
References	[1]. Mohammadi S, et al. Indole-3-carbinol induces G1 cell cycle arrest and apoptosis through aryl hydrocarbon receptor in THP-1 monocytic cell line.J Recept Signal Transduct Res. 2017 Oct;37(5):506-514. [2]. Safa M, et al. Indole-3-carbinol suppresses NF-κB activity and stimulates the p53 pathway in pre-B acute lymphoblastic leukemia cells. Tumour Biol. 2015 May;36(5):3919-30.

Density	1.3±0.1 g/cm3
Boiling Point	360.6±17.0 °C at 760 mmHg
Melting Point	96-99 °C(lit.)
Molecular Formula	C₉H₉NO
Molecular Weight	147.174
Flash Point	171.9±20.9 °C
Exact Mass	147.068420
PSA	36.02000
LogP	0.96
Vapour Pressure	0.0±0.8 mmHg at 25°C
Index of Refraction	1.705
Storage condition	2-8°C
Stability	2-80C

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NL9483000

CHEMICAL NAME :: Indole-3-methanol

CAS REGISTRY NUMBER :: 700-06-1

BEILSTEIN REFERENCE NO. :: 0121323

LAST UPDATED :: 199706

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C9-H9-N-O

MOLECULAR WEIGHT :: 147.19

WISWESSER LINE NOTATION :: T56 BMJ D1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Behavioral - coma

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 18,159,1980 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 9100 mg/kg/13W-I

TOXIC EFFECTS :: Liver - jaundice (or hyperbilirubinemia) hepatocellular Liver - changes in liver weight

REFERENCE :: TOXID9 Toxicologist. (Soc. of Toxicology, Inc., 475 Wolf Ledge Parkway, Akron, OH 44311) V.1- 1981- Volume(issue)/page/year: 15,292,1995

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 5600 mg/kg/13W-I

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: TOXID9 Toxicologist. (Soc. of Toxicology, Inc., 475 Wolf Ledge Parkway, Akron, OH 44311) V.1- 1981- Volume(issue)/page/year: 15,292,1995 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1 mg/kg

SEX/DURATION :: female 15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - delayed effects

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 141,68,1996

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 400 mg/kg

SEX/DURATION :: female 8-9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 18,159,1980

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H315-H319
Precautionary Statements	P305 + P351 + P338
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xi:Irritant
Risk Phrases	R36/38
Safety Phrases	S26-S36
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	NL9483000
HS Code	2933990090

Precursor 10
487-89-8 124-40-3 120-72-9 50-00-0
86204-54-8 17206-03-0 87-52-5 86204-60-6
87-51-4 5457-31-8
DownStream 9
487-89-8 5457-28-3 91-56-5 22546-09-4
83-34-1 4414-76-0 96551-22-3 771-50-6
771-51-7

HS Code	2933990090
Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%