10088. Xylulose

Nomenclature

CAS number: 5962-29-8
threo-Pentulose.
C5H10O5; mol wt 150.13.
C 40.00%, H 6.71%, O 53.29%.

Description and references

l-Form has been found in the urine of humans with pentosuria. Prepn of dl-form: Gascoigne, Chem. Ind. (London) 1959, 402; of d-form: Mendicino, J. Am. Chem. Soc. 82, 4975 (1960); of l-form: Wolfrom, Bennett, J. Org. Chem. 30, 458 (1965). Isoln of dl-form from the acid hydrolysate of bagasse hemicellulose: Banerjee et al., Sci. Cult. 27, 498 (1961), C.A. 56, 11682d (1962). Enzymic prepn of l-form: Hough, Jones, Chem. Ind. (London) 1952, 907; eidem, J. Chem. Soc. 1952, 4047. Formation of l-form in normal humans and guinea pigs, and its utilization by guinea-pig liver prepns: Touster et al., J. Am. Chem. Soc. 76, 5005 (1954). Reviews: The Carbohydrates, W. Pigman, Ed. (Academic Press, New York, 1957) pp 80, 86-87, 759, 795; Methods in Carbohydrate Chemistry vol. 1, R. L. Whistler, M. L. Wolfrom, Eds. (Academic Press, New York, 1962) pp 94-101.

Chemical structure

Derivative

d-Isomer.

Properties

Syrup. [α]D18 33° (c = 2.5).

Derivative

d-Isomer p-bromophenylhydrazone.
C11H15BrN2O4; mol wt 319.15.
C 41.40%, H 4.74%, Br 25.04%, N 8.78%, O 20.05%.

Properties

Pale yellow crystals from abs ethanol + water, mp 128-129°. [α]D20 +24° (15 min) → 31° (7 days, in pyridine).

Derivative

l-Isomer.

Properties

Syrup. [α]D21 +31°.

Derivative

l-Isomer p-bromophenylhydrazone.

Properties

Yellow plates from dil alc, mp 128°. [α]D20 20° (10 min) → +22° (5 hrs, c = 0.5 in ethanol).