Erythrulose

Erythrulose
IUPAC name (R)-1,3,4-Trihydroxybutan-2-one
Other names D-Erythrulose Glycerotetrulose
Identifiers
CAS number	496-55-9
PubChem	5460177
ChemSpider	4573812 Y
ChEBI	CHEBI:16023 Y
Jmol-3D images	Image 1 Image 2
SMILES OCC([C@H](O)CO)=O O=C(CO)[C@H](O)CO
InChI InChI=1S/C4H8O4/c5-1-3(7)4(8)2-6/h3,5-7H,1-2H2/t3-/m1/s1 Y Key: UQPHVQVXLPRNCX-GSVOUGTGSA-N Y InChI=1/C4H8O4/c5-1-3(7)4(8)2-6/h3,5-7H,1-2H2/t3-/m1/s1 Key: UQPHVQVXLPRNCX-GSVOUGTGBU
Properties
Molecular formula	C4H8O4
Molar mass	120.104g/mol
Appearance	Syrup
Solubility in water	Soluble
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

D-Erythrulose (also known as erythrulose) is a tetrose carbohydrate with the chemical formula C₄H₈O₄.^[1][2] It has one ketone group and so is part of the ketose family. It is used in some self-tanning cosmetics, in general, combined with dihydroxyacetone (DHA).^[3]

Erythrulose is a natural-based keto-sugar that reacts with the amino acids in the keratin protein on the outer or dead surface layer of the skin (the stratum corneum layer of the epidermis).^[4] This nontoxic^[5] reaction produces a temporary browning effect similar to the Maillard reaction. This is not a stain or dye, but rather a chemical reaction that produces a color change on all treated skin. The reaction is similar to the browning effect seen when a cut apple slice is exposed to oxygen.

The brown color is comparable to the appearance of a UV-based suntan. Because the skin continually exfoliates itself, losing thousands of dead surface skin cells each day, the tan hue is temporary. The tan appearance lasts from two to 10 days, depending on application type and skin condition.

Erythrulose is a clear to pale-yellowish liquid, which naturally occurs in red raspberries. According to the manufacturing company, Centerchem, Inc. [1], erythrulose is manufactured from the aerobic fermentation of the bacterium Gluconobacter, followed by extensive multi-step purification.

Erythrulose and dihydroxyacetone (DHA) are very similar in composition, and both react much the same way on the skin surface. Erythrulose produces a lighter and slower-developing tan, taking 24 to 48 hours to complete development. When used alone, it fades faster than a DHA-based sunless tan. Some people feel the final tone of erythrulose is slightly redder, and less bronze, than the DHA-based tan. It may be^{[weasel words]} less drying to the skin surface, helping provide a smoother fading tint. When combined with DHA, the resulting sunless tan is said^{[by whom?]} to last longer^{[citation needed]}, fade better^{[citation needed]}, and provide a more cosmetically pleasing^{[citation needed]} color tone. In sunless tanning products, it is incorporated at 1% to 3% levels.

Not all users develop a tan coloration from erythrulose; some may find their fading is more uneven and blotchy when this ingredient is used. Because of the added cost associated with this ingredient, some manufacturers feel it is an inefficient additive to the sunless tanning product line.

Individuals sensitive to DHA may be^{[weasel words]} able to use erythrulose as a skin-safe self-tanning replacement. Erythrulose is more expensive, and difficult^{[citation needed]} to obtain. Because DHA and erythrulose are very similar in composition, it is not unusual for someone to be sensitive to both DHA and erythrulose.

Erythrulose reacts on the skin's surface and does not^{[citation needed]} seem to^{[weasel words]} penetrate beyond the dead surface skin layers. Side effects are limited to^{[citation needed]} occasional contact dermatitis in sensitive individuals. In many suspected cases of sensitivity, the reaction is related to other ingredients in the self-tanning product, such as preservatives, dyes, fragrances, or plant-based additives and extracts.

Though erythrulose appears^{[weasel words]} safe for use by all indications, it is not currently approved by the Food and Drug Administration (FDA) as a self-tanning agent.

References

1. ^ Thisbe K. Lindhorst (2007). Essentials of Carbohydrate Chemistry and Biochemistry (1st ed.). Wiley-VCH. ISBN 3527315284. 
2. ^ John F. Robyt (1997). Essentials of Carbohydrate Chemistry (1st ed.). Springer. ISBN 0387949518. 
3. ^ A. N. Simonov, L. G. Matvienko, O. P. Pestunova, V. N. Parmon, N. A. Komandrova, V. A. Denisenko & V. E. Vas’kovskii. "Selective synthesis of erythrulose and 3-pentulose from formaldehyde and dihydroxyacetone catalyzed by phosphates in a neutral aqueous medium". Kinetics and Catalysis 48 (4): 550–555. doi:10.1134/S0023158407040118. http://www.springerlink.com/content/n4hg6l5368640h34/. 
4. ^ DE EP1704847, Kripp Thomas, Harpe Caroli, "Cosmetic agents and methods of mirrorizing keratin fibres", published 03/12/2008 
5. ^ Craig G. Burkhart & Craig N. Burkhart (2009). "Dihydroxyacetone and methods to improve its performance as artificial tanner". The Open Dermatology Journal 3: 42–43. http://www.benthamscience.com/open/todj/articles/V003/42TODJ.pdf.