3182. Dihydroxyacetone

Nomenclature

CAS number: 96-26-4
1,3-Dihydroxy-2-propanone; 1,3-dihydroxydimethyl ketone; Protosol; Ketochromin.
C3H6O3; mol wt 90.08.
C 40.00%, H 6.71%, O 53.28%.

Description and references

Produced from glycerol by Acetobacter sp. under aerobic conditions: Bernhauer, Schoen, Z. Physiol. Chem. 177, 107 (1928); Rutten, Rec. Trav. Chim. 70, 449 (1951); Bousfield et al., J. Inst. Brew. 53, 258 (1947); US 2948658 (1960 to Baxter). Review: Chem. Eng. News 38, 62 (Feb. 22, 1960), 54 (Aug. 15, 1960).

Chemical structure

Properties

Cryst powder; fairly hygroscopic; characteristic odor; sweet, cooling taste. mp about 75-80°. The normal form is a dimer, slowly sol in 1 part water, 15 parts alcohol. When freshly prepd reverts rapidly to monomer in soln. The monomer is very sol in water, alcohol, ether, acetone.

Use

Artificial tanning agent; active ingredient in Man-Tan; Oxatone; Tanorama; Q.T. (Quick Tan); Tan Tone; Magic Tan. Formulations: Barmak, Am. Perfum., March 1960, p 57; Andreadis, Miklean, US 2949403 (1960).