762. Arabitol

Nomenclature

CAS number: 2152-56-9
Arabinitol; 1,2,3,4,5-pentanepentol; arabite.
C5H12O5; mol wt 152.15.
C 39.47%, H 7.95%, O 52.58%.

Description and references

d-Form obtained by reduction of d-arabinose or d-lyxose with sodium amalgam: Ruff, Ber. 32, 555 (1899); Ruff, Ollendorff, Ber. 33, 1802 (1900); Bertrand, Bull. Soc. Chim. [3] 15, 593 (1896). Production by fermentation from molasses using Saccharomyces rouxii and Saccharomyces mellis: Lavin, Holloway, US 2934474 (1960 to Comm. Solvents). l-Form obtained by reduction of l-arabinose with sodium amalgam: Kiliani, Ber. 20, 1234, 1571 (1887). dl-Form obtained from equal parts of d- and l-arabitol: Ruff, loc. cit. Synthesis: Lespian, Compt. Rend. 206, 1773 (1938).

Chemical structure

Properties

Prisms from 90% alc. mp 105-106°. One part dissolves in 66 parts of 90% alc at 12°.

Derivative

d-Form.

Properties

Big prismatic crystals. Sweet taste. mp 103°. [α]D20 +7.7° (c = 9.26 in satd borax soln). Freely sol in water. One part dissolves in 48 parts of 90% alc at 12°.

Derivative

l-Form.

Properties

Wart-like crystals, sweet taste. mp 102°. Weakly levorotatory in satd borax soln. Freely sol in water and in boiling 90% alc. One part dissolves in 46 parts of 90% alc at 12°. Does not reduce Fehling's soln.

Derivative

Pentanitrate.
C5H7N5O15; mol wt 377.13.
C 15.92%, H 1.87%, N 18.57%, O 63.64%.

Properties

Sirup, sol in alcohol, ether, acetone. Strongly reduces Fehling's soln.