|Jmol-3D images||Image 1|
|Molar mass||90.078 g/mol|
89-91 °C, 362-364 K, 192-196 °F
|GHS signal word||WARNING|
|GHS hazard statements||H319|
|GHS precautionary statements||P264, P280, P305+351+338, P337+313|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
DHA is a hygroscopic white crystalline powder. It has a sweet cooling taste and a characteristic odor. It is the simplest of all ketoses and, having no chiral center, is the only one that has no optical activity. The normal form is a dimer which is slowly soluble in one part water and 15 parts ethanol. When freshly prepared, it reverts rapidly to the monomer in solution. The monomer is very soluble in water, ethanol, diethyl ether and acetone and toluene.
DHA may be prepared, along with glyceraldehyde, by the mild oxidation of glycerol, for example with hydrogen peroxide and a ferrous salt as catalyst. It can also be prepared in high yield and selectivity at room temperature from glycerol using cationic palladium-based catalysts with oxygen, air or benzoquinone acting as co-oxidants.   Glyceraldehyde is a structural isomer of dihydroxyacetone.
DHA was first recognized as a skin coloring agent by German scientists in the 1920s. Through its use in the X-ray process, it was noted as causing the skin surface to turn brown when spilled.
In the 1950s, Eva Wittgenstein at the University of Cincinnati did further research with dihydroxyacetone. Her studies involved using DHA as an oral drug for assisting children with glycogen storage disease. The children received large doses of DHA by mouth, and sometimes spat or spilled the substance onto their skin. Healthcare workers noticed that the skin turned brown after a few hours of DHA exposure.
Eva Wittgenstein continued to experiment with DHA, painting liquid solutions of it onto her own skin. She was able to consistently reproduce the pigmentation effect, and noted that DHA did not penetrate beyond the stratum corneum, or dead skin surface layer. Research then continued on DHA's skin coloring effect in relation to treatment for patients suffering from vitiligo.
This skin browning effect is non-toxic, and similar to the Maillard reaction. DHA reacts chemically with the amino acids in the skin, which are part of the protein containing keratin layer on the skin surface. Various amino acids react differently to DHA, producing different tones of coloration from yellow to brown. The resulting pigments are called melanoidins. These are similar in coloration to melanin, the natural substance in the deeper skin layers which brown or "tan", from exposure to UV rays.
Both acetic acid bacteria A. aceti and G. oxydans use glycerol as a carbon source to form dihydroxyacetone. DHA is formed by ketogenesis of glycerol. It can affect the sensory quality of the wine with sweet/etherish properties. DHA can also react with proline to produce a "crust-like" aroma. Dihydroxyacetone can affect the anti-microbial activity in wine, as it has the ability to bind SO2.
Sunless tanning 
Coppertone introduced the first consumer sunless tanning lotion into the marketplace in the 1960s. This product was called “Quick Tan” or “QT”. It was sold as an overnight tanning agent, and other companies followed with similar products. Consumers soon tired of this product due to unattractive results such as orange palms, streaking and poor coloration. Because of the QT experience, many people today still associate sunless tanning with fake-looking orange tans.
By the 1980s, new sunless tanning formulations appeared on the market and refinements in the DHA manufacturing process created products that produced a more natural looking color and better fading. Consumer concerns surrounding damage associated with UV tanning options spurred further popularity of sunless tanning products as an alternative to UV tanning. Dozens of brands appeared on drugstore shelves, in numerous formulations.
Today, DHA is the main active ingredient in all sunless tanning skincare preparations. It may be used alone or combined with other tanning components such as erythrulose. DHA is considered the most effective sun-free tanning additive.
Sunless tanning products contain DHA in concentrations ranging from 1% to 15%. Most drugstore products range from 3% to 5%, with professional products ranging from 5% to 15%. The percentages correspond with the product coloration levels from light to dark. Lighter products are more beginner-friendly, but may require multiple coats to produce the desired color depth. Darker products produce a dark tan in one coat, but are also more prone to streaking, unevenness, or off-color tones. The artificial tan takes 2 to 4 hours to begin appearing on the skin surface, and will continue to darken for 24 to 72 hours, depending on formulation type.
Once the darkening effect has occurred, the tan will not sweat off or wash away with soap or water. It will fade gradually over 3 to 10 days, in conjunction with the skin's normal exfoliation process. Exfoliation, prolonged water submersion, or heavy sweating can lighten the tan, as these all contribute to rapid dead skin cell exfoliation (the dead skin cells are the tinted portion of the sunless tan.)
Current sunless tanners are formulated into sprays, lotions, gels, mousses, and cosmetic wipes. Professional applied products include spray tanning booths, airbrush tan applications, and hand applied lotions, gels, mousses and wipes.
DHA safety considerations 
DHA has been approved for cosmetic use by the FDA, the Canadian Health Ministry, and most of the EU member nations. DHA-based sunless tanning has been recommended by the Skin Cancer Foundation, American Academy of Dermatology Association, Canadian Dermatology Association and the American Medical Association as a safer alternative to sun-bathing. The European Commission's Scientific Committee on Consumer Safety has issued a comprehensive Opinion on DHA in which after considerable review concluded that spray tanning with DHA solutions did not pose risk to the consumer.
Some studies, however, have suggested possible risk. One study showed that [pig] skin treated with 20% DHA for forty minutes had 180% additional free radicals formed during sun exposure compared with untreated skin. Another self-tanner ingredient, erythrulose, produced a similar response at high levels. Although it is unclear what layer of skin (dermis or epidermis) these free radicals were present in, it may be prudent to take extra care in avoiding sun exposure or using sunscreen for a period of time (duration unknown) after application. An antioxidant cream might also minimize free radical production.
The study by Jung et al. further confirms earlier results demonstrating that dihydroxyacetone in combination with dimethylisosorbide enhances the process of (sun-based) tanning. This earlier study also found that dihydroxyacetone also has an effect on the amino acids and nucleic acids which is bad for the skin. The free radicals are due to the generation of AGE (Advanced Glycation Products) such as amadori products (a type of AGE) as a result of the reaction of DHA with the skin. AGEs are behind the damage to the skin that occurs with high blood sugar in diabetes where similar glycation occurs.
There is some additional evidence that (live) cells exposed to DHA may be damaged  This may be of more concern for incidental inhalation and mucosal exposure during spray tanning rather than manually applying cream externally to (dead) skin. The FDA approved DHA for external use in 1973, and has made precautionary recommendations for consumer protection in spray tanning applications. (A June 2012 ABC consumer report claimed the main chemical found inside that spray - DHA - is potentially hazardous when inhaled. Physicians interviewed in the report expressed safety concerns. The ABC report did not permit a fair opportunity for rebuttal evidence.)
Although some self-tanners contain sunscreen, its effect will not last as long as the tan. The skin browning of a sunless tan may provide some UV protection (up to SPF 3), but this low-level protection should be supplemented with additional protection. There may also be some inhibition of vitamin D production in DHA-treated skin.
Contact dermatitis is rarely reported, and a recent study showed that DHA causes severe contact dermatitis in Mexican hairless dogs. Most cases of sensitivity are due to other ingredients in the skin product preparation, such as preservatives, plant extracts, dyes or fragrances.
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|url=missing title (help), retrieved 2009-09-03.
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- Painter, R. M., Pearson, D. M. and Waymouth, R. M. (2010), Selective Catalytic Oxidation of Glycerol to Dihydroxyacetone. Angewandte Chemie International Edition, 49: 9456–9459. doi: 10.1002/anie.201004063.
- Chung, K., Banik, S. M., De Crisci, A. G., Pearson, D. M., Blake, T. R., Olsson, J. V., Ingram, A. J., Zare, R. N., Waymouth, R. M. (2013), Chemoselective Pd-Catalyzed Oxidation of Polyols: Synthetic Scope and Mechanistic Studies, Journal of the American Chemical Soceity, ASAP, doi: 10.1021/ja4008694
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- Eva Wittgenstein and DHA
- WITTGENSTEIN E, GUEST GM (1961). "Biochemical effects of dihydroxyacetone". J. Invest. Dermatol. 37 (5): 421–6. doi:10.1038/jid.1961.137. PMID 14007781.
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- Code of Federal Regulations, Title 21, Volume 1, §73.1150 Listing of color additives exempt from certification
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- Petersen AB, Wulf HC, Gniadecki R, Gajkowska B. Dihydroxyacetone, the active browning ingredient in sunless tanning lotions, induces DNA damage, cell-cycle block and apoptosis in cultured HaCaT keratinocytes. Mutat Res. 2004 Jun 13;560(2):173-86.
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- Petersen AB, Na R, Wulf HC. Sunless skin tanning with dihydroxyacetone delays broad-spectrum ultraviolet photocarcinogenesis in hairless mice. Mutat Res. 2003 Dec 9;542(1-2):129-38.
- Armas LA, Fusaro RM, Sayre RM, Huerter CJ, Heaney RP. Do melanoidins induced by topical 9% dihydroxyacetone sunless tanning spray inhibit vitamin d production? A pilot study. Photochem Photobiol. 2009 Sep-Oct;85(5):1265-6.
- Morren M, Dooms-Goossens A, Heidbuchel M, et al. Contact allergy to dihydroxyacetone. Contact Dermatitis 1991; 25: 326-7
- Kimura T. "Contact dermatitis caused by sunless tanning treatment with dihydroxyacetone in hairless descendants of Mexican hairless dogs." Environ Toxicol. 2008 Nov 17. 
- How Stuff Works
- US FDA/CFSAN - Tanning Pills
- American Academy of Dermatology on Self Tanners
- DHA and Vitiligo
- DHA as a Vitiligo option
- Self Tanning lotions as a skin safe alternative to UV tanning
- The American Cancer Society on Sunless Tanners
- New Zealand Dermatological Society recommends sunless tanners