Dihydroxyacetone
Names | |
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Preferred IUPAC name
1,3-Dihydroxypropan-2-one | |
Other names
1,3-Dihydroxypropanone
Dihydroxyacetone DHA Glycerone | |
Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard
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100.002.268 |
EC Number |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties[1] | |
C3H6O3 | |
Molar mass | 90.078 g·mol−1 |
Melting point | 89 to 91 °C (192 to 196 °F; 362 to 364 K) |
Hazards[2] | |
GHS labelling: | |
Warning | |
H319 | |
P264, P280, P305+P351+P338, P337+P313 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dihydroxyacetone (
3H
6O
3.
DHA is primarily used as an ingredient in
Chemistry
DHA is a
This skin browning effect is attributed to a
Biochemistry
Its phosphorylated form, dihydroxyacetone phosphate (DHAP), takes part in glycolysis, and it is an intermediate product of fructose metabolism.
Preparation
DHA may be prepared, along with
DHA can be derived from plants.[5]
Sunless tanning
DHA is the main active ingredient in many sunless tanning skincare preparations, which may be classified as topical sunless tanner or temporary bronzers. As opposed to bronzers containing pigment to coat the skin, DHA bronzers cause a coloration of the surface layer of the skin and do not wash off easily. Current sunless tanners are formulated into sprays, lotions, gels, mousses, and cosmetic wipes.[5] Professional applied products include spray tanning booths, airbrush tan applications, and hand applied lotions, gels, mousses and wipes. Lotions often last longer than sprays but may cause blotching and streaking. Mousses and gels tend to dry faster. Mousses generally contain less moisture.[5]
Lotion manufacturers also produce a wide variety of sunless tanning preparations that replace DHA with natural bronzing agents such as
Sunless tanning products contain DHA in concentrations ranging from 1% to 20%. Most drugstore products range from 3% to 5%, with professional products ranging from 5% to 20%. 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.[5]
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 7 days as a result of the regular skin exfoliation. Scrubbing the skin, 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).[5]
It is recommended to shave, wash, or exfoliate the skin before application in order to produce a more even tan. The skin should not be moisturized before application except very dry areas. Application should be done evenly with a circular motion.[5]
Bronzers contain DHA in concentrations from 1 to 15% allowing to adjust the intensity of coloration. DHA formulations have improved in several ways since the introduction in the 1960s.[5]
Safe use and side effects
The
DHA-containing spray tans have been associated to side effects such as rashes, cough, dizziness, and fainting. Frequent exposure to spray tans may increase the risk of pulmonary disease, asthma, chronic obstructive pulmonary disease (COPD), and cancer. [5]
The chemical reaction of DHA in the skin may lead to an unpleasent smell. Often fragrances are added to the formulation to mask the smell. Fragrances may lead to allergic reactions or worsen asthma symptoms. Some products contain
Frequent use of DHA containing products may to be problematic due to a number of side effects. A FDA report concluded that 11 percent of the applied DHA may penetrate into the living cells of the epidermis and dermis. A previous study linked DHA to DNA damage, cell-cycle block, and apoptosis in living cells. Skin coloring induced by frequent use of DHA may interfere with vitamin D production in the skin cells which depends on the exposure to UVB in sunlight. Topical DHA use in levels of more than 5% seem to increase free-radical damage from sunlight for 24 hours after application. Antioxidants may be added to the formulation to produce a more natural tan, and may potentially counteract free radical damage. The use of sunless tanning products may increase the likelihood of sunburn as the artificial coloration of the skin interferes with the natural adaption of the skin to sun exposure. The tanning induced by DHA has been rated with a low sun protection factor (SPF) of 3. It can therefore not replace the application of a regular suncreen before exposing the skin to intensive sunlight.[5]
DHA may be contained in moisturizers with added fruit extracts sold as "maximizers". Tanning agents labelled as "tingles" contain benzyl nicotinate which presumably aids the production of melanin by increasing blood circulation in the skin, thus supplying more oxygen to melanocytes, and often induces a burning or tingling feeling. The effect of products called "optimizers" or "accelerators" containing the protein tyrosine as a precursor in the production of melanin is disputed.[5]
History
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.
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 suit 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 still associate sunless tanning with fake-looking orange tans.[citation needed]
In the 1970s the
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 (
Winemaking
Both acetic acid bacteria Acetobacter aceti and Gluconobacter oxydans use glycerol as a carbon source to form dihydroxyacetone. DHA is formed by ketogenesis of glycerol.[15] 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.[15][16][17] Dihydroxyacetone can affect the anti-microbial activity in wine, as it has the ability to bind SO2.[18]
References
- ISBN 0-8493-0462-8..
- ^ HSNO Chemical Classification Information Database, New Zealand Environmental Risk Management Authority, retrieved 3 September 2009
- ISBN 0911910123, 3225
- ^ PMID 1479107.
- ^ a b c d e f g h i j k l m n Garone M, Howard J, Fabrikant J. A review of common tanning methods. J Clin Aesthet Dermatol. 2015 Feb;8(2):43-7. PMID: 25741402; PMCID: PMC4345932.
- PMID 21031380.
- PMID 23659308.
- .
- .
- PMID 14007781.
- PMID 13706567.
- S2CID 7946691.
- ^ "Are 'Spray-On' Tans Safe? Experts Raise Questions as Industry Puts Out Warnings". ABC News.
- ^ 21 CFR 73.1150
- ^ a b Drysdale, G.S.; Fleet, G.H. (1988). "Acetic acid bacteria in winemaking: a review". American Journal of Enology and Viticulture. 39 (2): 143–154.
- ISBN 978-0-398-04083-3.[page needed]
- ISBN 978-0-8342-1270-1.[page needed]
- .
External links
- How Stuff Works
- US FDA/CFSAN - Tanning Pills
- American Academy of Dermatology on Self Tanners
- DHA and Vitiligo
- Fesq, H.; Brockow, K.; Strom, K.; Mempel, M.; Ring, J.; Abeck, D. (2001). "Dihydroxyacetone in a New Formulation – A Powerful Therapeutic Option in Vitiligo". Dermatology. 203 (3): 241–3. S2CID 26802465.
- Draelos, Zoe D. (2002). "Self-Tanning Lotions: Are They a Healthy Way to Achieve a Tan?". American Journal of Clinical Dermatology. 3 (5): 317–8. S2CID 53819152.
- New Zealand Dermatological Society recommends sunless tanners