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C1305

Sigma-Aldrich

Cafestol acetate

≥98%

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About This Item

Empirical Formula (Hill Notation):
C22H30O4
CAS Number:
81760-48-7
Molecular Weight:
358.47
MDL number:
MFCD00133152
UNSPSC Code:
12352205
PubChem Substance ID:
24892399
NACRES:
NA.79

Assay

≥98%

form

powder

technique(s)

HPLC: suitable

color

white to off-white

storage temp.

2-8°C

SMILES string

CC(=O)OCC1(O)CC23CCC4c5ccoc5CCC4(C)C2CCC1C3

InChI

1S/C22H30O4/c1-14(23)26-13-22(24)12-21-9-5-17-16-7-10-25-18(16)6-8-20(17,2)19(21)4-3-15(22)11-21/h7,10,15,17,19,24H,3-6,8-9,11-13H2,1-2H3

InChI key

PTGGVIKFNQSFBY-UHFFFAOYSA-N

Application

Cafestol acetate has been used to determine the effects of coffee on heat shock response (HSR).

Biochem/physiol Actions

Cafestol is a coffee-specific diterpene. It has anti-carcinogenic and anti-inflammatory activities. Cafestol stimulates apoptosis in cells associated with colorectal and renal cancer (Caki cells). It is used to study mechanisms of anti-oxidation related to hydrogen peroxide induced oxidative stress and DNA damage. Cafestol increases the level of glutathione (GSH), by stimulating γ-glutamylcysteine synthetase. It acts as a chemopreventive agent by inducing cytochrome P-450.

Other Notes

Furan-containing diterpene from green coffee beans.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Wolfgang W Huber et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 46(4), 1230-1238 (2007-11-07)
Coffee drinking appears to reduce cancer risk in liver and colon. Such chemoprevention may be caused by the diterpenes kahweol and cafestol (K/C) contained in unfiltered beverage. In animals, K/C treatment inhibited the mutagenicity/tumorigenicity of several carcinogens, likely explicable by
Use of silver nitrate impregnated silica cartridges in the separation of kahweol and cafestol esters by preparative liquid chromatography.
L K Lam et al.
Journal of chromatography, 328, 422-424 (1985-06-28)
Agnieszka Potęga et al.
Journal of pharmaceutical analysis, 10(4), 376-384 (2020-09-15)
5-Dimethylaminopropylamino-8-hydroxytriazoloacridinone (C-1305) is a promising antitumor compound developed in our laboratory. A better understanding of its metabolic transformations is still needed to explain the multidirectional mechanism of pharmacological action of triazoloacridinone derivatives at all. Thus, the aim of the current
Cafestol, a diterpene molecule found in coffee, induces leukemia cell death
Lima C, et al.
Biomedicine and Pharmacotherapy, 92, 1045-1054 (2017)
Ting Shen et al.
Biological & pharmaceutical bulletin, 33(1), 128-132 (2010-01-05)
Coffee is a popular beverage worldwide with various nutritional benefits. Diterpene cafestol, one of the major components of coffee, contributes to its beneficial effects through various biological activities such as chemopreventive, antitumorigenic, hepatoprotective, antioxidative and antiinflammatory effects. In this study
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