3420. Dopa

Nomenclature

3-Hydroxytyrosine; 3-(3,4-dihydroxyphenyl)alanine; β-(3,4-dihydroxyphenyl)-α-alanine; 2-amino-3-(3,4-dihydroxyphenyl)propanoic acid.
C9H11NO4; mol wt 197.19.
C 54.82%, H 5.62%, N 7.10%, O 32.45%.

Description and references

An amino acid found in seedlings, pods and beans of Vicia faba L. (broad beans) Stizolobium deeringianum L. (velvet beans) Leguminosae: Torquati, Arch. farm. sper. 15, 213, 308 (1913), C.A. 7, 2774 (1913); Sealock, Biochemical Preparations vol. 1, 25 (1949). Absolute configuration: Guggenheim, Z. Physiol. Chem. 88, 276 (1913). Prepn of dl-, d-, and l-dopa: Yamada et al., Chem. Pharm. Bull. 10, 693 (1962).

Chemical structure

Derivative

dl-Form.

Nomenclature

CAS number: 63-84-3

Properties

Prisms from water or from aq NaHSO3 soln, dec 270-272°. Soly in water: 144 mg/40 ml. Readily sol in dil acids and alkalies; slightly sol in benzene, carbon disulfide. Practically insol in abs alcohol, ether, glacial acetic acid, petr ether, chloroform. Oxidizes readily.

Derivative

d-Form.

Nomenclature

CAS number: 5796-17-8

Properties

Needles from water, dec 276-278°. [α]D11 +13.0° (c = 5.27 in 1N HCl). Soly in water: 66 mg/40 ml.

Derivative

l-Form see Levodopa.