Title: Hamamelose
CAS Registry Number: 4573-78-8
CAS Name: 2-C-(Hydroxymethyl)-D-ribose
Molecular Formula: C6H12O6
Molecular Weight: 180.16
Percent Composition: C 40.00%, H 6.71%, O 53.28%
Literature References: From tannin of witch hazel (Hamamelis virginiana L., Hamamelidaceae): Fischer, Freudenberg, Ber. 45, 2709 (1912); Freudenberg, Peters, ibid. 53, 953 (1920); Anderson, U.S.A.E.C. UCRL-8870, 114 (1959). Structure: Schmidt, Ann. 476, 250 (1929). Configuration: Schmidt, Heintz, ibid. 515, 77 (1934). Synthesis: Novák, Sorm, Collect. Czech. Chem. Commun. 30, 3303 (1965); Paulsen et al., Ber. 105, 1978 (1972). Synthesis of L-hamamelose: Burton et al., Proc. Chem. Soc. London 1962, 181. Synthesis and 1H, 13C NMR study of aqueous equilibrium: W. A. Szarek et al., Can. J. Chem. 61, 461 (1983).
Derivative Type: D-Form
Properties: Crystals from abs ethanol, mp 111°. [a]D21 -7.4° (equilib in water).
Melting point: mp 111°
Optical Rotation: [a]D21 -7.4° (equilib in water)
Derivative Type: L-Form
Properties: Crystals from ethanol + ethyl acetate, mp 110-111°. [a]D22 +1.3° (3 min) ® +7.3° (equilib after 17 min).
Melting point: mp 110-111°
Optical Rotation: [a]D22 +1.3° (3 min) ® +7.3° (equilib after 17 min)
|