78824-30-3

Basic information

• Product Name: garcinol
• Synonyms: garcinol;(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;(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;Camboginol
• CAS NO: 78824-30-3
• Molecular Formula: C₃₈H₅₀O₆
• Molecular Weight: 602.36
• EINECS: 200-258-5
• Mol File: 78824-30-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: 132 °C
• Boiling Point: 710.763 °C at 760 mmHg
• Flash Point: 397.609 °C
• Appearance: /
• Density: 1.114 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.563
• Storage Temp.: ?20°C
• Solubility: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
• PKA: 4.50±1.00(Predicted)
• 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.
• CAS DataBase Reference: garcinol(CAS DataBase Reference)
• NIST Chemistry Reference: garcinol(78824-30-3)
• EPA Substance Registry System: garcinol(78824-30-3)

Safety Data

• Hazardous Substances Data: 78824-30-3(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 78824-30-3 differently. You can refer to the following data:
1. 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.
2. Garcinol is a small molecule inhibitor of histone acetyltransferases. Used in cancer therapy. Garcinol, harvested from Garcinia indica.

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

InChI:InChI=1/C38H50O6/c1-22(2)11-13-27(25(7)8)20-37-21-28(15-12-23(3)4)36(9,10)38(35(37)44,18-17-24(5)6)34(43)31(33(37)42)32(41)26-14-16-29(39)30(40)19-26/h11-12,14,16-17,19,27-28,39-40,42H,7,13,15,18,20-21H2,1-6,8-10H3/t27-,28+,37+,38-/m0/s1

Upstream product

• 2214-15-5 4-(cyanocarbonyl)-1,2-phenylene diacetate 

Downstream Products

• 71117-97-0 cambogin 
• 2010216-41-6 GDPPH-1 

Relevant articles and documents

Stereodivergent Strategy in Structural Determination: Asymmetric Total Synthesis of Garcinol, Cambogin, and Related Analogues

The asymmetric total synthesis of five biologically significant polycyclic polyprenylated acylphloroglucinols (PPAPs), including garcinol and cambogin, was achieved through a highly diastereoselective and stereodivergent strategy. Along the way, an efficient cascade Dieckmann cyclization was employed to construct the bicyclo[3.3.1]nonane core in one step. The synthesis provided a general approach toward the chiral endo-type B PPAPs and their C-30 diastereomers in a single sequence, which resolved the challenges of the absolute configuration determination/structural revision of PPAPs bearing exocyclic stereocenters.