4278. d-Fucose

Nomenclature

CAS number: 3615-37-0
6-Deoxy-d-galactose; d-galactomethylose; rhodeose.
C6H12O5; mol wt 164.16.
C 43.90%, H 7.37%, O 48.73%.

Description and references

Obtained from glucosides found in various species of Convolvulaceae, e.g., convolvulin, jalapin, β-turpethein. Isoln: Votocek, Z. Zuckerind. Boehm. 24, 249; Chem. Zentralbl. 1901, I, 1042; 1902, II, 1361; 1905, II, 1528. Isoln from jalap resin: Votocek, Bulir, ibid. 1906, I, 1818. Prepn by acid hydrolysis of chartreusin: Sternbach et al., J. Am. Chem. Soc. 80, 1639 (1958).

Chemical structure

Properties

α-Form, needles from alc. Sweet taste. mp 144°. Shows mutarotation, [α]D19 +127.0° (7 min) → +89.4° (31 min) → +77.2° (71 min) → +76.0° (final value 146 min, c = 10). Soluble in water; moderately sol in alcohol.

Derivative

Pentaacetate.
C16H22O10; mol wt 374.34.
C 51.34%, H 5.92%, O 42.74%.

Properties

mp 115.5°.

Derivative

Oxime.
C6H13NO5; mol wt 179.17.
C 40.22%, H 7.31%, N 7.82%, O 44.65%.

Properties

mp 188.5°.

Derivative

Phenylhydrazone.
C12H18N2O4; mol wt 254.28.
C 56.68%, H 7.14%, N 11.02%, O 25.17%.

Properties

mp 172°.

Derivative

Phenylosazone.
C18H22N4O3; mol wt 342.39.
C 63.14%, H 6.48%, N 16.36%, O 14.02%.

Properties

mp 176.5°.