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°

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