Cafestol

Title: Cafestol
CAS Registry Number: 469-83-0
CAS Name: [3bS-(3ba,5ab,7b,8b,10aa,10bb)]-3b,4,5,6,7,8,9,10,10a,10b,11,12-Dodecahydro-7-hydroxy-10b-methyl-5a,8-methano-5aH-cyclohepta[5,6]naphtho[2,1-b]furan-7-methanol
Additional Names: cafesterol
Molecular Formula: C20H28O3
Molecular Weight: 316.43
Percent Composition: C 75.91%, H 8.92%, O 15.17%
Literature References: Diterpenoid constituent of coffee. Isoln from green coffee oil: Slotta, Neisser, Ber. 71, 1991, 2342 (1938); C. Djerassi et al., J. Org. Chem. 18, 1449 (1953). Prepn and purification: R. Bertholet, US 4692534 (1987 to Nestec). Structure: C. Djerassi et al., J. Am. Chem. Soc. 81, 2386 (1959); R. A. Finnegan, C. Djerassi, ibid. 82, 4342 (1960). Stereochemical studies: R. A. Finnegan, J. Org. Chem. 26, 3057 (1961); A. I. Scott et al., J. Am. Chem. Soc. 84, 3197 (1962); A. I. Scott et al., Tetrahedron 20, 1339 (1964). Stereospecific total synthesis of (±)-form: E. J. Corey et al., J. Am. Chem. Soc. 109, 4717 (1987).
Properties: Crystals from hexane, mp 158°-l60°. [a]D -101°. uv max: 222 nm (log e 3.78).
Melting point: mp 158°-l60°
Optical Rotation: [a]D -101°
Absorption maximum: uv max: 222 nm (log e 3.78)
Derivative Type: Acetate
Molecular Formula: C22H30O4
Molecular Weight: 358.47
Percent Composition: C 73.71%, H 8.44%, O 17.85%
Properties: Needles from petr ether, mp 167-168°. [a]D -89°. uv max: 222 nm (log e 3.80).
Melting point: mp 167-168°
Optical Rotation: [a]D -89°
Absorption maximum: uv max: 222 nm (log e 3.80)
Derivative Type: Tetrahydrocafestol
Molecular Formula: C20H32O3
Molecular Weight: 320.47
Percent Composition: C 74.96%, H 10.06%, O 14.98%
Properties: Crystals from dil methanol, mp 154.5-157°.
Melting point: mp 154.5-157°
Caffeic Acid Calamus Calcimycin Calcineurin Calcipotriene

Cafestol
Cafestol.svg
Identifiers
CAS number 469-83-0
PubChem 108052
ChemSpider 10289419
UNII AC465T6Q6W
KEGG C09066
Jmol-3D images Image 1
Properties
Molecular formula C20H28O3
Molar mass 316.43 g mol−1
Melting point 158 to 162 °C; 316 to 324 °F; 431 to 435 K
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Cafestol is a diterpene molecule present in coffee.

A typical bean of Coffea arabica contains about 0.6% cafestol by weight. Cafestol is present in highest quantity in unfiltered coffee drinks such as French press coffee or Turkish coffee/Greek coffee. In filtered coffee drinks such as drip brewed coffee, it is present in only negligible amounts.

Studies have shown that regular consumption of boiled coffee increases serum cholesterol by 8% in men and 10% in women. For those drinking filter coffee, the effect was only significant for women.[1]