| Identification | Back Directory | [Name]
garcinol | [CAS]
78824-30-3 | [Synonyms]
garcinol
Camboginol
(1R,5R,7R)-3-(3,4-Dihydroxybenzyol)-4-hydroxy-8,8-dimethyl-1,7-bis(3-methyl-2-buten-1-yl)-5-[(2S)-5-methyl-2-(1-methylethenyl)-4-hexen-1-yl]bicyclo[3.3.1]non-3-ene-2,9-dione
(1R,5R,7R)-3-(3,4-Dihydroxybenzoyl)-4-hydroxy-8,8-dimethyl-1,7-bis(3-methyl-2-buten-1-yl)-5-[(2S)-5-methyl-2-(1-methylethenyl)-4-hexen-1-yl]-Bicyclo[3.3.1]non-3-ene-2,9-dione
Bicyclo[3.3.1]non-3-ene-2,9-dione, 3-(3,4-dihydroxybenzoyl)-4-hydroxy-8,8-dimethyl-1,7-bis(3-methyl-2-buten-1-yl)-5-[(2S)-5-methyl-2-(1-methylethenyl)-4-hexen-1-yl]-, (1R,5R,7R)-
(1R,3E,5R,7R)-3-[(3,4-dihydroxyphenyl)-hydroxy-methylidene]-8,8-dimethyl-1,7-bis(3-methylbut-2-enyl)-5-[(2S)-5-methyl-2-prop-1-en-2-yl-hex-4-enyl]bicyclo[3.3.1]nonane-2,4,9-trione | [EINECS(EC#)]
200-258-5 | [Molecular Formula]
C38H50O6 | [MDL Number]
MFCD03700761 | [MOL File]
78824-30-3.mol | [Molecular Weight]
602.8 |
| Chemical Properties | Back Directory | [Melting point ]
132 °C | [Boiling point ]
710.8±60.0 °C(Predicted) | [density ]
1.114±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml). | [form ]
Yellow solid. | [pka]
4.50±1.00(Predicted) | [color ]
Yellow | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month. Garcinol is prone to oxidation. Protect from exposure to air. | [LogP]
11.546 (est) |
| Hazard Information | Back Directory | [Description]
Garcinol (78824-30-3) is a HAT (histone acetyltransferase) inhibitor (p300 IC50=7 μM and PCAF IC50=5 μM) both in vitro and in vivo.1 It potentiates TRAIL-induced apoptosis of cancer cells. In cancer cells garcinol, independent of the cell type, induces both of the TRAIL receptors, death receptor 4 (DR4) and DR5. Garcinol neither induces the receptors of normal cells nor sensitizes them to TRAIL.2 | [Uses]
Garcinol is an inhibitor of the histone acetyltransferases (HATs) p300 and PCAF (IC50 = 7 and 5 μM, respectively). It also inhibits the HAT GCN5 in Cryptococcus neoformans, inducing temperature sensitivity and impairing growth. A polyisoprenylated benzophenone isolated from Garcinia indica, garcinol promotes neurogenesis and ex vivo expansion of human hematopoietic stem cells. Moreover, it induces apoptosis in several types of cancer cells and has anti-inflammatory actions. | [Definition]
ChEBI: Garcinol is a monoterpenoid. | [in vivo]
Garcinol (i.p.; 1 and 2 mg/kg; five times/week for 4 consecutive weeks) induces significant inhibition of tumor growth[3].
| Animal Model: | Five-week-old athymic nu/nu male mice bearing subcutaneous CAL27 tumors[3] | | Dosage: | 1 and 2 mg/kg | | Administration: | I.p.; five times/week for 4 consecutive weeks | | Result: | Induced significant inhibition of tumor growth.
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| [IC 50]
AChE; BChE; GCN5/PCAF; Human Endogenous Metabolite | [storage]
Store at -20°C,protect from light | [References]
1) Balasubramanyam, et al.; (2004) Polyisoprenylated benzophenone, garcinol, a natural histone acetyltransferase inhibitor, represses chromatin transcription and alters global gene expression; J. Biol. Chem. 279 33716
2) Prasad, et al. (2010) Garcinol potentiates TRAIL-induced apoptosis through modulation of death receptors and antiapoptotic proteins; Mol. Cancer Ther. 9 856 |
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