| Identification | Back Directory | [Name]
KAHWEOL | [CAS]
6894-43-5 | [Synonyms]
KAHWEOL
KAHWEOL USP/EP/BP
Kahweol
DISCONTINUED, unstable
(3bS)-3b,4,5,6,7,8,9,10,10aα,10b-Decahydro-7β-hydroxy-10bβ-methyl-5aβ,8β-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-decahydro-7-hydroxy-10b-methyl-,(3bS,5aS,7R,8R,10aR,10bS)-
[3bS-(3balpha,5abeta,7beta,8beta,10aalpha,10bbeta)]-3b,4,5,6,7,8,9,10,10a,10b-Decahydro-7-hydroxy-10b-methyl-5a,8-methano-5aH-cyclohepta[5,6]naphtho[2,1-b]furan-7-methanol | [Molecular Formula]
C20H26O3 | [MDL Number]
MFCD00171665 | [MOL File]
6894-43-5.mol | [Molecular Weight]
314.42 |
| Chemical Properties | Back Directory | [Melting point ]
88-90℃ | [Boiling point ]
476.6±45.0 °C(Predicted) | [density ]
1.25±0.1 g/cm3(Predicted) | [storage temp. ]
−20°C | [solubility ]
DMF:5.0(Max Conc. mg/mL);0.64(Max Conc. mM)
DMSO:18.17(Max Conc. mg/mL);57.77(Max Conc. mM)
Ethanol:5.0(Max Conc. mg/mL);0.64(Max Conc. mM)
Ethanol:PBS (pH 7.2) (1:5):0.02(Max Conc. mg/mL);0.06(Max Conc. mM) | [form ]
White to off-white solid. | [pka]
14.43±0.40(Predicted) | [color ]
Off-white to light yellow | [Major Application]
food and beverages | [InChI]
1S/C20H26O3/c1-18-7-5-16-14(6-9-23-16)15(18)4-8-19-10-13(2-3-17(18)19)20(22,11-19)12-21/h5-7,9,13,15,17,21-22H,2-4,8,10-12H2,1H3/t13-,15-,17+,18-,19+,20+/m1/s1 | [InChIKey]
JEKMKNDURXDJAD-HWUKTEKMSA-N | [SMILES]
CC12C=Cc3occc3C1CCC45CC(CCC24)C(O)(CO)C5 | [LogP]
3.380 (est) |
| Hazard Information | Back Directory | [Uses]
Kahweol is an antioxidant diterpene contained in unfiltered coffee. Kahweol behaves as an anti-inflammatory and anti-angiogenic compound with potential use in antitumoral therapies. Recent research have demonstrated the ability of Kahweol in inhibiting metastasis by modulating expressions of MMPs and VEGF via STAT3 inactivation. | [Definition]
ChEBI: Kahweol is a diterpenoid with formula C20H26O3, isolated from the beans of Coffea arabica. It exhibits antioxidant, anti-inflammatory, anti-angiogenesis and anti-proliferative properties. It has a role as an angiogenesis inhibitor, an apoptosis inducer, an antioxidant, an anti-inflammatory agent, an antineoplastic agent and a plant metabolite. It is a diterpenoid, a member of furans, an organic heteropentacyclic compound, a tertiary alcohol and a primary alcohol. | [Biological Activity]
Induces glutathione S-transferase. Has anti-cancer, chemoprotective, anti-inflammatory and anti-atherosclerotic properties. |
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