Indole-3-carbinol Struktur

3-Hydroxymethylindol

Bezeichnung:3-Hydroxymethylindol

CAS-Nr700-06-1

Englisch Name:Indole-3-carbinol

CBNumberCB7295605

SummenformelC9H9NO

Molgewicht147.17

MOL-Datei700-06-1.mol

Synonyma

3-Hydroxymethylindol

3-Hydroxymethylindol physikalisch-chemischer Eigenschaften

Schmelzpunkt	96-99 °C (lit.)
Siedepunkt	267.28°C (rough estimate)
Dichte	1.1135 (rough estimate)
Brechungsindex	1.5670 (estimate)
storage temp.	2-8°C
Löslichkeit	soluble in Methanol
Aggregatzustand	Crystalline Powder or Flakes
pka	15.10±0.10(Predicted)
Farbe	Off-white to yellow-orange
BRN	121323
Stabilität	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 Datenbank	700-06-1(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/38
S-Sätze:	26-36
WGK Germany	3
RTECS-Nr.	NL9483000
Hazard Note	Irritant
HS Code	29339900

Gefahreninformationscode (GHS)

Indole-3-carbinol Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/38:Reizt die Augen und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
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).
Verwenden
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.
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.
synthetische
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%.
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
Allgemeine Beschreibung
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 Upstream-Materialien And Downstream Produkte

3-Hydroxymethylindol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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