Dihydroxyacetone

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Contents

Dihydroxyacetone
1,3-dihydroxypropan-2-one 200.svg
Dihydroxyacetone 3D ball.png
Names
Preferred IUPAC name
1,3-Dihydroxypropan-2-one
Other names
1,3-Dihydroxypropanone
Dihydroxyacetone
DHA
Glycerone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.002.268 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-494-5
KEGG
PubChem CID
UNII
  • InChI=1S/C3H6O3/c4-1-3(6)2-5/h4-5H,1-2H2 Yes check.svgY
    Key: RXKJFZQQPQGTFL-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C3H6O3/c4-1-3(6)2-5/h4-5H,1-2H2
    Key: RXKJFZQQPQGTFL-UHFFFAOYAE
  • O=C(CO)CO
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:
GHS-pictogram-exclam.svg
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Dihydroxyacetone ( /ˌdhˌdrɒksiˈæsɪtn/ ; DHA), also known as glycerone, is a simple saccharide (a triose) with formula C
3
H
6
O
3
.

DHA is primarily used as an ingredient in sunless tanning products. It is often derived from plant sources such as sugar beets and sugar cane, and by the fermentation of glycerin.

Chemistry

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 has no chiral center. The normal form is a dimer (2,5-bis(hydroxymethyl)-1,4-dioxane-2,5-diol). The dimer slowly dissolves in water, [3] whereupon it converts to the monomer. These solutions are stable at pH's between 4 and 6. In more basic solution, it degrades to brown product. [4]

DHA dimer monomer.svg

This skin browning effect is attributed to a Maillard reaction. DHA condenses with the amino acid residues in the protein keratin, the major component of the skin surface. When injected, no pigmentation occurs, consistent with a role for oxygen in color development. [4] The resulting pigments, which can be removed by abrasion, 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. [5]

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 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. [6] [7] [8] Glyceraldehyde is a structural isomer of dihydroxyacetone.

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 black walnut shell. DHA may be used alone or combined with other tanning components such as erythrulose. DHA is considered the most effective sun-free tanning additive.[ citation needed ]

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 United States Food and Drug Administration (FDA) has approved DHA for topical application on the skin, but not for contact with eyes, lips, and mucous membranes. DHA may not be used in spray tanning booths due to risk of exposure of these sensitive areas. [5]

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 unpleasant smell. Fragrances are often added to the formulation to mask the smell, which may lead to allergic reactions or worsen asthma symptoms. Some products contain parabens as chemical preservatives that can cause rosacea and allergic contact dermatitis and act as weak estrogens. [5]

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 sunscreen before exposing the skin to intensive sunlight. [5]

Erythrulose is a similar agent contained in red raspberries that produces a short-lived reddish tan. The general tanning effect is usually improved when used in combination with DHA. Erythrulose also increases the occurrence of free radicals. [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. [9] [10] [11] [12] 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. 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 appear to penetrate beyond the stratum corneum, or dead skin surface layer (the FDA eventually concluded this is not entirely true [13] ). Research then continued on DHA's skin coloring effect in relation to treatment for patients with vitiligo.

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 United States Food and Drug Administration (FDA) added DHA permanently to their list of approved cosmetic ingredients. [14]

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 (sunbathing, indoor tanning) spurred popularity of sunless tanning products as an alternative to UV tanning. Dozens of brands appeared on drugstore shelves, in numerous formulations.[ citation needed ]

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]

Related Research Articles

<span class="mw-page-title-main">Cosmetics</span> Substances applied to the body to change appearance or fragrance

Cosmetics are composed of mixtures of chemical compounds derived from either natural sources or synthetically created ones. Cosmetics have various purposes, including personal and skin care. They can also be used to conceal blemishes and enhance natural features. Makeup can also add colour to a person's face, enhance a persons features or change the appearance of the face entirely to resemble a different person, creature, or object.

<span class="mw-page-title-main">Sunscreen</span> Topical skin product that helps protect against sunburn

Sunscreen, also known as sunblock, sun lotion or sun cream, is a photoprotective topical product for the skin that helps protect against sunburn and prevent skin cancer. Sunscreens come as lotions, sprays, gels, foams, sticks, powders and other topical products. Sunscreens are common supplements to clothing, particularly sunglasses, sunhats and special sun protective clothing, and other forms of photoprotection.

<span class="mw-page-title-main">Sun tanning</span> Darkening of skin in response to ultraviolet light

Sun tanning or tanning is the process whereby skin color is darkened or tanned. It is most often a result of exposure to ultraviolet (UV) radiation from sunlight or from artificial sources, such as a tanning lamp found in indoor tanning beds. People who deliberately tan their skin by exposure to the sun engage in a passive recreational activity of sun bathing. Some people use chemical products that can produce a tanning effect without exposure to ultraviolet radiation, known as sunless tanning.

<span class="mw-page-title-main">Indoor tanning</span> Tanning using an artificial source of ultraviolet light

Indoor tanning involves using a device that emits ultraviolet radiation to produce a cosmetic tan. Typically found in tanning salons, gyms, spas, hotels, and sporting facilities, and less often in private residences, the most common device is a horizontal tanning bed, also known as a sunbed or solarium. Vertical devices are known as tanning booths or stand-up sunbeds.

<span class="mw-page-title-main">Ultraviolet light therapy</span> Form of treatment for skin disorders

Ultraviolet light therapy or ultraviolet phototherapy is a treatment for psoriasis, atopic skin disorder, vitiligo and other skin diseases.

<span class="mw-page-title-main">Erythrulose</span> Chemical compound

D-Erythrulose (also known as erythrulose) is a tetrose carbohydrate with the chemical formula C4H8O4. 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).

<span class="mw-page-title-main">Sunless tanning</span> Indoor tanning lotion

Sunless tanning, also known as UV filled tanning, self tanning, spray tanning, or fake tanning, refers to the effect of a suntan without exposure to the Sun. Sunless tanning involves the use of oral agents (carotenids), or creams, lotions or sprays applied to the skin. Skin-applied products may be skin-reactive agents or temporary bronzers (colorants).

Natural skin care uses topical creams and lotions made of ingredients available in nature. Much of the recent literature reviews plant-derived ingredients, which may include herbs, roots, flowers and essential oils, but natural substances in skin care products include animal-derived products such as beeswax, and minerals. These substances may be combined with various carrier agents, preservatives, surfactants, humectants and emulsifiers.

<span class="mw-page-title-main">Lotion</span> Skin treatment preparation

Lotion is a low-viscosity topical preparation intended for application to the skin. By contrast, creams and gels have higher viscosity, typically due to lower water content. Lotions are applied to external skin with bare hands, a brush, a clean cloth, or cotton wool.

<span class="mw-page-title-main">Skin care</span> Range of practices that support skin integrity

Skin care or skincare is a range of practices that support skin integrity, enhance its appearance, and relieve skin conditions. They can include nutrition, avoidance of excessive sun exposure, and appropriate use of emollients. Practices that enhance appearance include the use of cosmetics, botulinum, exfoliation, fillers, laser resurfacing, microdermabrasion, peels, retinol therapy, and ultrasonic skin treatment. Skin care is a routine daily procedure in many settings, such as skin that is either too dry or too moist, and prevention of dermatitis and prevention of skin injuries.

<span class="mw-page-title-main">Amcinonide</span> Chemical compound

Amcinonide is a topical glucocorticoid used to treat itching, redness and swelling associated with several dermatologic conditions such as atopic dermatitis and allergic contact dermatitis. Amcinonide can also be classified as a multi-functional small molecule corticosteroid, which has been approved by the FDA and is currently marketed as an ointment, lotion, or cream. It acts as both a transcription factor for responses to glucocorticoids and modulator for other transcription factors while also regulating phospholipase A2 activity.

<span class="mw-page-title-main">Indoor tanning lotion</span>

Indoor tanning lotions accelerate the tanning process, by promoting the production of melanin. Increasing blood flow to the skin is a proposed mechanism, which may in turn stimulate production of melanin by melanocytes. Historically, indoor tanning lotions have contained no sunscreen and offer no protection from the sun. However, many tanning lotions currently contain sunscreen. Unlike sunless tanning lotions, these are designed for use with an ultraviolet source such as a tanning bed or booth.

Tanning activators are chemicals that increase the effect of UV-radiation on the human skin.

<span class="mw-page-title-main">Phytophotodermatitis</span> Medical condition

Phytophotodermatitis, also known as berloque dermatitis, margarita photodermatitis, lime disease or lime phytodermatitis is a cutaneous phototoxic inflammatory reaction resulting from contact with a light-sensitizing botanical agent followed by exposure to ultraviolet A (UV-A) light. Symptoms include erythema, edema, blisters, and delayed hyperpigmentation. Heat and moisture tend to exacerbate the reaction.

<span class="mw-page-title-main">Afamelanotide</span> Chemical compound

Afamelanotide, sold under the brand name Scenesse, is a medication used to prevent phototoxicity and to reduce pain from light exposure for people with erythropoietic protoporphyria. It is a melanocortin 1 receptor (MC1-R) agonist and a synthetic peptide and analogue of α-melanocyte stimulating hormone. It is administered as subcutaneous implant.

<span class="mw-page-title-main">Bergapten</span> Chemical compound

Bergapten (5-methoxypsoralen) is a naturally-occurring organic chemical compound produced by numerous plant species, especially from the carrot family Apiaceae and the citrus family Rutaceae. For example, bergapten has been extracted from 24 species of the genus Heracleum in the family Apiaceae. In the family Rutaceae, various Citrus species contain significant amounts of bergapten, especially the bergamot orange, the micrantha, and certain varieties of lime and bitter orange.

<span class="mw-page-title-main">Sunburn</span> Burning of the skin by the suns radiation

Sunburn is a form of radiation burn that affects living tissue, such as skin, that results from an overexposure to ultraviolet (UV) radiation, usually from the Sun. Common symptoms in humans and other animals include red or reddish skin that is hot to the touch or painful, general fatigue, and mild dizziness. Other symptoms include blistering, peeling skin, swelling, itching, and nausea. Excessive UV radiation is the leading cause of (primarily) non-malignant skin tumors, which in extreme cases can be life-threatening. Sunburn is an inflammatory response in the tissue triggered by direct DNA damage by UV radiation. When the cells' DNA is overly damaged by UV radiation, type I cell-death is triggered and the tissue is replaced.

Bain de Soleil was a brand of sunscreen that was produced by Bayer. It was affiliated with the Coppertone brand. The name Bain de Soleil is French for "sun bathing." The brand used the slogan "Welcome to a place more colorful." In the 1970s and 1980s, the brand used the slogan "Bain de Soleil, for the St. Tropez tan." The brand was discontinued in December 2019.

Palm Beach Tan is a chain of indoor tanning facilities based in Dallas, Texas. Founded in 1990, it is the largest indoor tanning chain in the United States, with over 460 locations under the Palm Beach Tan, Palm Beach Tan Sunless, and Planet Tan brands. Sunbed tanning lotions and spray tanning lotions are the two products offered by them.

Tanning may refer to:

References

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  14. 21 CFR 73.1150
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