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G5173

Sigma-Aldrich

Garcinol

≥95%

Synonym(s):

(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

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About This Item

Empirical Formula (Hill Notation):
C38H50O6
CAS Number:
78824-30-3
Molecular Weight:
602.80
MDL number:
MFCD03700761
UNSPSC Code:
12352200
PubChem Substance ID:
329799938

Assay

≥95%

form

powder

color

yellow

solubility

>5 mg/mL

storage temp.

−20°C

SMILES string

C\C(C)=C\C[C@@H](C[C@@]12C[C@@H](C\C=C(\C)C)C(C)(C)[C@@](C\C=C(/C)C)(C(=O)C(=C1O)C(=O)c3ccc(O)c(O)c3)C2=O)C(C)=C

InChI

1S/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

InChI key

QDKLRKZQSOQWJQ-SMDXAGPFSA-N

Biochem/physiol Actions

Garcinol is a HAT (histone acetyltransferase) inhibitor. Garcinol is anti-inflammatory and anti-carcinogenic. Histone acetyltransferases provide opposing enzymatic mechanisms for chromatin remodeling and epigenetic control of gene expression. HATs are involved in regulation of transformation, transcription, differentiation, apoptosis, embryonic development and oncogenesis. IC50 p300 = 7 mM; IC50 PCAF = 5 mM (similar to anacardic acid). Garcinol is highly toxic compared to LTK-14, and does not discriminate between p300 and PCAF.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Zaorui Zhao et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 32(7), 2344-2351 (2012-03-08)
Histone acetylation has recently been implicated in learning and memory processes, yet necessity of histone acetylation for such processes has not been demonstrated using pharmacological inhibitors of histone acetyltransferases (HATs). As such, the present study tested whether garcinol, a potent
Aamir Ahmad et al.
Molecular cancer therapeutics, 11(10), 2193-2201 (2012-07-24)
Anticancer properties of Garcinia indica-derived garcinol are just beginning to be elucidated. We have earlier reported its cancer cell-specific induction of apoptosis in breast cancer cells, which was mediated through the downregulation of NF-κB signaling pathway. To gain further mechanistic
Aamir Ahmad et al.
Carcinogenesis, 33(12), 2450-2456 (2012-09-14)
Garcinol, obtained from Garcinia indica, has exhibited some promising anticancer activity. In particular, our earlier work has demonstrated its ability to inhibit cell proliferation and induction of apoptosis in multiple cancer cell lines representative of breast, prostate, as well as
Taito Nishino et al.
PloS one, 6(9), e24298-e24298 (2011-09-21)
Human cord blood (hCB) is the main source of hematopoietic stem and progenitor cells (HSCs/PCs) for transplantation. Efforts to overcome relative shortages of HSCs/PCs have led to technologies to expand HSCs/PCs ex vivo. However, methods suitable for clinical practice have
Mansi A Parasramka et al.
Molecular nutrition & food research, 57(2), 235-248 (2013-01-08)
Alterations in microRNA (miRNA/miR) genes are of biological importance in the pathophysiology of cancers, including pancreatic cancer (PaCa). Although growing evidence supports the role of miRNA in cancer, their response to dietary phytochemicals is less known. Previously, we showed that
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