| Identification | Back Directory | [Name]
CAFESTOL | [CAS]
469-83-0 | [Synonyms]
CAFESTOL
CAFESTEROL
Ccris 1518
CAFESTOL(SH)
Cafestol (>85%)
3bα,4,5,6,7,8,9,10,10aα,10b,11,12-Dodecahydro-7β-hydroxy-10bβ-methyl-5aβ,8β-methano-5aH-cyclohepta[5,6]naphtho[2,1-b]furan-7α-methanol
(3bS,5aS,7R,8R,10aR,10bS)-3b,4,5,6,7,8,9,10,10a,10b,11,12-Dodecahydro-7-hydroxy-10b-methyl-5a,8-methano-5aH-cyclohepta[5,6]naphtho[2,1-b]furan-7-methanol
5A,8-Methano-5ah-cyclohepta(5,6)naphtho(2,1-B)furan-7-methanol, 3B,4,5,6,7,8,9,10,10A,10B,11,12-dodecahydro-7-hydroxy-10B-methyl-, (3bs,5as,7R,8R,10ar,10bs)-
5A,8-Methano-5ah-cyclohepta(5,6)naphtho(2,1-B)furan-7-methanol, 3B,4,5,6,7,8,9,10,10A,10B,11,12-dodecahydro-7-hydroxy-10B-methyl-, (3bs-(3balpha,5abeta,7beta,8beta,10aalpha,10bbeta))- | [Molecular Formula]
C20H28O3 | [MDL Number]
MFCD01075769 | [MOL File]
469-83-0.mol | [Molecular Weight]
316.43 |
| Chemical Properties | Back Directory | [Melting point ]
160-162℃ (分解) (ethyl ether pentane ) | [alpha ]
D -101° | [Boiling point ]
468.6±45.0 °C(Predicted) | [density ]
1.23±0.1 g/cm3 (20 ºC 760 Torr) | [RTECS ]
PB9185090 | [storage temp. ]
-20°C Freezer, Under inert atmosphere | [solubility ]
Soluble in dichlormethane, DMSO or ethanol | [form ]
White to off-white solid. | [pka]
14.44±0.40(Predicted) | [color ]
Off-White to Light Beige | [optical activity]
-9724 (CHCl3) | [LogP]
4.234 (est) |
| Hazard Information | Back Directory | [Uses]
Cafestol is a diterpene molecule that displays anti-carcinogenic properties in studies. | [Definition]
ChEBI: Cafestol is an organic heteropentacyclic compound and furan diterpenoid with formula C20H28O3 obtained from the unsaponifiable fraction of coffee oil (a lipid fraction obtained from coffee beans by organic solvent extraction). It has a role as a plant metabolite, an apoptosis inducer, a hypoglycemic agent, an angiogenesis inhibitor, an antineoplastic agent, an antioxidant and an anti-inflammatory agent. It is an organic heteropentacyclic compound, a tertiary alcohol, a diterpenoid, a member of furans and a primary alcohol. | [in vivo]
Cafestol (40-80 mg/kg; oral gavage ; 20 days) has antitumor effect in xenografted mouse model of colon cancer[3].
Cafestol (0.4-1.1 mg/day; feed administration; 10 weeks) shows antidiabetic activity in KKAy mice[4]. | Animal Model: | HCT116 cells treated BALB/C null mice[3] | | Dosage: | 40 and 80 mg/kg | | Administration: | Oral gavage (i.g.); 20 days | | Result: | Increased the body weight, tumor suppression rate and decreased the tumor weight.
Did not change the colonic morphology.
Increased the richness and diversity of intestinal flora in tumor-bearing mice.
Stimulated autophagy in the colon tumors.
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| Animal Model: | Male KKAy mice[4] | | Dosage: | 0.4 and 1.1 mg/day | | Administration: | Feed administration; 10 weeks | | Result: | Reduced fasting plasma glucose and increased insulin secretion.
Reduced fasting glucagon was 20% lower and insulin sensitivity improved by 42% at dose of 1.1 mg.
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| [IC 50]
COX-2; NF-κB; ERK2 | [storage]
4°C, protect from light |
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