4608. Hamamelose

Nomenclature

CAS number: 4573-78-8
2-C-(Hydroxymethyl)-d-ribose.
C6H12O6; mol wt 180.16.
C 40.00%, H 6.71%, O 53.28%.

Description and 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).

Chemical structure

Derivative

d-Form.

Properties

Crystals from abs ethanol, mp 111°. [α]D21 7.4° (equilib in water).

Derivative

l-Form.

Properties

Crystals from ethanol + ethyl acetate, mp 110-111°. [α]D22 +1.3° (3 min) → +7.3° (equilib after 17 min).