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P0020

Sigma-Aldrich

Pristimerin

Synonym(s):

(9b,13a,14b,20a)-3-Hydroxy-9,13-dimethyl-2-oxo-24,25,26 -trinoroleana-1(10),3,5,7-tertraen-29-oic acid methyl ester, Celastrol methyl ester

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About This Item

Empirical Formula (Hill Notation):
C30H40O4
CAS Number:
1258-84-0
Molecular Weight:
464.64
MDL number:
MFCD01711331
UNSPSC Code:
12352200
PubChem Substance ID:
329819975
NACRES:
NA.77

Assay

≥98% (HPLC)

Quality Level

100

form

powder

storage condition

protect from light

color

orange

solubility

DMSO: ≥5 mg/mL

storage temp.

−20°C

SMILES string

COC(=O)[C@]1(C)CC[C@]2(C)CC[C@]3(C)C4=CC=C5C(C)=C(O)C(=O)C=C5[C@]4(C)CC[C@@]3(C)C2C1

InChI

1S/C30H40O4/c1-18-19-8-9-22-28(4,20(19)16-21(31)24(18)32)13-15-30(6)23-17-27(3,25(33)34-7)11-10-26(23,2)12-14-29(22,30)5/h8-9,16,23,32H,10-15,17H2,1-7H3/t23-,26-,27-,28+,29-,30+/m1/s1

InChI key

JFACETXYABVHFD-WXPPGMDDSA-N

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Application

Pristimerin has been used as an anti-tumor agent to study its effects on conditionally reprogrammed patient-derived lung adenocarcinoma cells (CRLCs). It has also been used as an anti-tumor agent to study its effects on conditionally reprogrammed patient derived-primary hepatocellular carcinoma cells (CRHCs).

Biochem/physiol Actions

More active than euphol against MGL, better activity with rat neurons, but less selective relative to similar enzymes.
More active than euphol against MGL, better activity with rat neurons, but less selective relative to similar enzymes. First MGL inhibitor to act reversibly, several others covalently bind to cysteine residues. Other studies involve multiply mylome, pristimerin inhibits NF-κB activation via inhibition of IKK-α or IKK-β. It is the methyl ester of celastrol (C0869).
Pristimerin is a quinone methide triterpenoid found abundantly in Celastraceae and Hippocrateaceae families. It shows anti-inflammatory, anti-malarial, anti-bacterial, and insecticidal properties. Pristimerin exhibits anti-cancer and anti-proliferative activity by affecting vasculogenesis, apoptosis, autophagy, migration, and invasion of tumor cells. It has been studied to exhibit therapeutic effects against leukemia, glioma, breast cancer, prostate cancer, oral cancer, and lung cancer.

Features and Benefits

This compound is featured on the Cannabinoid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000175201
0000175202
0000151114
0000151114
0000175202

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Rodger E Tiedemann et al.
Blood, 113(17), 4027-4037 (2008-12-20)
As multiple myeloma tumors universally dysregulate cyclin D genes we conducted high-throughput chemical library screens for compounds that induce suppression of cyclin D2 promoter transcription. The top-ranked compound was a natural triterpenoid, pristimerin. Strikingly, the early transcriptional response of cells
Patricia Marçal da Costa et al.
Toxicology in vitro : an international journal published in association with BIBRA, 22(4), 854-863 (2008-02-26)
Pristimerin has been shown to be cytotoxic to several cancer cell lines. In the present work, the cytotoxicity of pristimerin was evaluated in human tumor cell lines and in human peripheral blood mononuclear cells (PBMC). This work also examined the
Hiroshi Morita et al.
Bioorganic & medicinal chemistry letters, 18(3), 1050-1052 (2008-01-01)
Four cytotoxic quinoid triterpenes, tingenone (1), 22 beta-hydroxytingenone (2), pristimerin (3), and celastrol (4), isolated from Maytenus chuchuhuasca, potently inhibit the polymerization of tubulin.
Chin-Chung Wu et al.
Molecular cancer therapeutics, 4(8), 1277-1285 (2005-08-12)
Pristimerin, a naturally occurring triterpenoid, has been shown to cause cytotoxicity in several cancer cell lines. However, the mechanism for the cytotoxic effect of pristimerin was never explored. In the present study, human breast cancer MDA-MB-231 cells treated with pristimerin
Pristimerin synergistically sensitizes conditionally reprogrammed patient derived-primary hepatocellular carcinoma cells to sorafenib through endoplasmic reticulum stress and ROS generation by modulating Akt/FoxO1/p27kip1 signaling pathway
Tang Y, et al.
Phytomedicine, 153563-153563 (2021)
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