Erythrulose

Last updated
Erythrulose
D-erythrulose.png
D-Erythrulose
DL-Erythrulose.svg
Names
IUPAC name
D-glycero-Tetrulose
Systematic IUPAC name
(3R)-1,3,4-Trihydroxybutan-2-one
Other names
Glycerotetrulose, erythrulose
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.129.795 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C4H8O4/c5-1-3(7)4(8)2-6/h3,5-7H,1-2H2/t3-/m1/s1 Yes check.svgY
    Key: UQPHVQVXLPRNCX-GSVOUGTGSA-N Yes check.svgY
  • InChI=1/C4H8O4/c5-1-3(7)4(8)2-6/h3,5-7H,1-2H2/t3-/m1/s1
    Key: UQPHVQVXLPRNCX-GSVOUGTGBU
  • OCC([C@H](O)CO)=O
  • O=C(CO)[C@H](O)CO
Properties
C4H8O4
Molar mass 120.104 g·mol−1
AppearanceSyrup
Soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

D-Erythrulose (also known as erythrulose) is a tetrose carbohydrate with the chemical formula C 4 H 8 O 4. [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/DHA reacts with the amino acids in the proteins of the first layers of skin (the stratum corneum and epidermis). One of the pathways involves free radicals at one of the steps of the Maillard reaction, [4] [5] distantly related to the browning effect when a cut apple slice is exposed to oxygen. The other pathway is the conventional Maillard reaction; both pathways are involved in the browning during food preparation and storage. This is not a stain or dye, but rather a chemical reaction that produces a color change on all treated skin. It does not involve the underlying skin pigmentation nor does it require exposure to ultraviolet light to initiate the color change. However, the 'tan' produced by erythrulose/DHA only has an SPF of up to 3, [6] [7] and enhances the free radical injury from UV (compared to untreated skin) for the 24 hours after self-tanner is applied, according to a 2007 study led by Katinka Jung of the Gematria Test Lab in Berlin. [8] Forty minutes after the researchers treated skin samples with high levels of erythrulose, they found that more than 140 percent additional free radicals formed during sun exposure compared with untreated skin. [8]

DHA produced similar results, but faster; however erythrulose takes longer to develop its full effect, therefore it lasts longer. For a day after self-tanner application, excessive sun exposure should be avoided and sunscreen should be worn outdoors, they say[ who? ]; an antioxidant cream could also minimize free radical production. Although some self-tanners contain sunscreen, its effect will not last as long as the tan. During UV irradiation free radicals, mainly superoxide/hydroperoxyl (O2•−/HO2•), and other reactive species (ROS/RNS) are produced, that can react with the ketoamines (Amadori products) and other intermediates of the Maillard reaction. This leads to autoxidation radical chain reactions of the ketoamines, which cause a dramatic increase in the radical injury of the skin. This can be suppressed by antioxidants, which shows involvement of reactive oxygen species (ROS). [9] The ketoamines were shown to cause DNA strand breaks and to act as mutagens. [10]

The free radicals are due to the action of UV light on AGE (advanced glycation end-products) as a result of the reaction of DHA with the skin, and the intermediates, such as Amadori products (a type of AGE), that lead to them. AGEs absorb UV light, but do not have melanin's extended electronic structure that dissipates the energy, so part of it goes towards starting free radical chain reactions instead, in which other AGEs participate readily. AGEs are behind the damage to the skin that occurs with high blood sugar in diabetes where similar glycation occurs. [11] [12] [13] [14]

Erythrulose is a clear to pale-yellowish liquid, which naturally occurs in red raspberries. According to one method, it is made through aerobic fermentation by the bacterium Gluconobacter, followed by extensive multi-step purification.[ citation needed ]

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.[ citation needed ]

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.

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[ citation needed ] self-tanning replacement. Erythrulose is more expensive, and difficult[ citation needed ] to obtain.

Erythrulose is not currently approved by the Food and Drug Administration (FDA) as a self-tanning agent.

Related Research Articles

<span class="mw-page-title-main">Ultraviolet</span> Energetic, invisible light energy range

Ultraviolet (UV) light is electromagnetic radiation of wavelengths of 10–400 nanometers, shorter than that of visible light, but longer than X-rays. UV radiation is present in sunlight, and constitutes about 10% of the total electromagnetic radiation output from the Sun. It is also produced by electric arcs, Cherenkov radiation, and specialized lights, such as mercury-vapor lamps, tanning lamps, and black lights.

<span class="mw-page-title-main">Maillard reaction</span> Chemical reaction that gives browned food flavor

The Maillard reaction is a chemical reaction between amino acids and reducing sugars to create melanoidins, the compounds that give browned food its distinctive flavor. Seared steaks, fried dumplings, cookies and other kinds of biscuits, breads, toasted marshmallows, falafel and many other foods undergo this reaction. It is named after French chemist Louis Camille Maillard, who first described it in 1912 while attempting to reproduce biological protein synthesis. The reaction is a form of non-enzymatic browning which typically proceeds rapidly from around 140 to 165 °C. Many recipes call for an oven temperature high enough to ensure that a Maillard reaction occurs. At higher temperatures, caramelization and subsequently pyrolysis become more pronounced.

<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">Dihydroxyacetone</span> Chemical compound

Dihydroxyacetone, also known as glycerone, is a simple saccharide with formula C
3H
6O
3.

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

Pyridoxamine (PM) is one form of vitamin B6. Chemically it is based on a pyridine ring structure, with hydroxyl, methyl, aminomethyl, and hydroxymethyl substituents. It differs from pyridoxine by the substituent at the 4-position. The hydroxyl at position 3 and aminomethyl group at position 4 of its ring endow pyridoxamine with a variety of chemical properties, including the scavenging of free radical species and carbonyl species formed in sugar and lipid degradation and chelation of metal ions that catalyze Amadori reactions.

Glycation is the covalent attachment of a sugar to a protein, lipid or nucleic acid molecule. Typical sugars that participate in glycation are glucose, fructose, and their derivatives. Glycation is the non-enzymatic process responsible for many complications in diabetes mellitus and is implicated in some diseases and in aging. Glycation end products are believed to play a causative role in the vascular complications of diabetes mellitus.

<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).

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

Methylglyoxal (MGO) is the organic compound with the formula CH3C(O)CHO. It is a reduced derivative of pyruvic acid. It is a reactive compound that is implicated in the biology of diabetes. Methylglyoxal is produced industrially by degradation of carbohydrates using overexpressed methylglyoxal synthase.

<span class="mw-page-title-main">UV filter</span> Camera parts, features and technologies

UV filters are compounds, mixtures, or materials that block or absorb ultraviolet (UV) light. One of the major applications of UV filters is their use as sunscreens to protect skin from sunburn and other sun/UV related damage. After the invention of digital cameras changed the field of photography, UV filters have been used to coat glass discs fitted to camera lenses to protect hardware that is sensitive to UV light.

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

Glucosepane is a lysine-arginine protein cross-linking product and advanced glycation end product (AGE) derived from D-glucose. It is an irreversible, covalent cross-link product that has been found to make intermolecular and intramolecular cross-links in the collagen of the extracellular matrix (ECM) and crystallin of the eyes. Covalent protein cross-links irreversibly link proteins together in the ECM of tissues. Glucosepane is present in human tissues at levels 10 to 1000 times higher than any other cross-linking AGE, and is currently considered to be the most important cross-linking AGE.

<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.

The Amadori rearrangement is an organic reaction describing the acid or base catalyzed isomerization or rearrangement reaction of the N-glycoside of an aldose or the glycosylamine to the corresponding 1-amino-1-deoxy-ketose. The reaction is important in carbohydrate chemistry, specifically the glycation of hemoglobin.

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

Pentosidine is a biomarker for advanced glycation endproducts, or AGEs. It is a well characterized and easily detected member of this large class of compounds.

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

<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.

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

Argpyrimidine is an organic compound with the chemical formula C11H18N4O3. It is an advanced glycation end-product formed from arginine and methylglyoxal through the Maillard reaction. Argpyrimidine has been studied for its food chemistry purposes and its potential involvement in aging diseases and diabetes mellitus.

Tanning may refer to:

References

  1. ↑ Lindhorst, Thisbe K. (2007). Essentials of Carbohydrate Chemistry and Biochemistry (1st ed.). Wiley-VCH. ISBN   978-3-527-31528-4.[ page needed ]
  2. ↑ Robyt, John F. (1997). Essentials of Carbohydrate Chemistry (1st ed.). Springer. ISBN   0-387-94951-8.[ page needed ]
  3. ↑ Simonov, A. N.; Matvienko, L. G.; Pestunova, O. P.; Parmon, V. N.; Komandrova, N. A.; Denisenko, V. A.; Vas’Kovskii, V. E. (2007). "Selective synthesis of erythrulose and 3-pentulose from formaldehyde and dihydroxyacetone catalyzed by phosphates in a neutral aqueous medium". Kinetics and Catalysis. 48 (4): 550–5. doi:10.1134/S0023158407040118. S2CID   84265261.
  4. ↑ Namiki, Mitsuo; Hayashi, Tateki (1983). "A New Mechanism of the Maillard Reaction Involving Sugar Fragmentation and Free Radical Formation". In Waller, George R.; Feather, Milton S. (eds.). The Maillard Reaction in Foods and Nutrition. ACS Symposium Series. Vol. 215. pp. 21–46. doi:10.1021/bk-1983-0215.ch002. ISBN   0-8412-0769-0.
  5. ↑ Roberts, Richard L.; Lloyd, Roger V. (1997). "Free Radical Formation from Secondary Amines in the Maillard Reaction". Journal of Agricultural and Food Chemistry. 45 (7): 2413–8. doi:10.1021/jf960902c.
  6. ↑ Faurschou, A.; Wulf, H.C. (2004). "Durability of the sun protection factor provided by dihydroxyacetone". Photodermatology, Photoimmunology and Photomedicine. 20 (5): 239–42. doi:10.1111/j.1600-0781.2004.00118.x. PMID   15379873. S2CID   35465870.
  7. ↑ Petersen, Anita B; Na, Renhua; Wulf, Hans Christian (2003). "Sunless skin tanning with dihydroxyacetone delays broad-spectrum ultraviolet photocarcinogenesis in hairless mice". Mutation Research/Genetic Toxicology and Environmental Mutagenesis. 542 (1–2): 129–38. Bibcode:2003MRGTE.542..129P. doi:10.1016/j.mrgentox.2003.09.003. PMID   14644361.
  8. 1 2 Jung, K.; Seifert, M.; Herrling, Th.; Fuchs, J. (2008). "UV-generated free radicals (FR) in skin: Their prevention by sunscreens and their induction by self-tanning agents". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 69 (5): 1423–8. Bibcode:2008AcSpA..69.1423J. doi:10.1016/j.saa.2007.09.029. PMID   18024196.
  9. ↑ Petersen, Anita B; Wulf, Hans Christian; Gniadecki, Robert; Gajkowska, Barbara (2004). "Dihydroxyacetone, the active browning ingredient in sunless tanning lotions, induces DNA damage, cell-cycle block and apoptosis in cultured HaCaT keratinocytes". Mutation Research/Genetic Toxicology and Environmental Mutagenesis. 560 (2): 173–86. Bibcode:2004MRGTE.560..173P. doi:10.1016/j.mrgentox.2004.03.002. PMID   15157655.
  10. ↑ Pischetsrieder, Monika; Seidel, Wolfgang; Münch, Gerald; Schinzel, Reinhard (1999). "N2-(1-Carboxyethyl)deoxyguanosine, a Nonenzymatic Glycation Adduct of DNA, Induces Single-Strand Breaks and Increases Mutation Frequencies". Biochemical and Biophysical Research Communications. 264 (2): 544–9. doi:10.1006/bbrc.1999.1528. PMID   10529399.
  11. ↑ Oak, Jeong-Ho; Nakagawa, Kiyotaka; Miyazawa, Teruo (2000). "Synthetically prepared Amadori-glycated phosphatidylethanolamine can trigger lipid peroxidation via free radical reactions". FEBS Letters. 481 (1): 26–30. Bibcode:2000FEBSL.481...26O. doi: 10.1016/S0014-5793(00)01966-9 . PMID   10984609. S2CID   23265125.
  12. ↑ Ramasamy, Ravichandran; d'Agati, Shi; Schmidt, Vivette; Ramasamy, Ann (2007). "Receptor for Advanced Glycation Endproducts (RAGE): A Formidable Force in the Pathogenesis of the Cardiovascular Complications of Diabetes & Aging". Current Molecular Medicine. 7 (8): 699–710. doi:10.2174/156652407783220732. PMID   18331228.
  13. ↑ Goldin, A.; Beckman, JA; Schmidt, AM; Creager, MA (2006). "Advanced Glycation End Products: Sparking the Development of Diabetic Vascular Injury". Circulation. 114 (6): 597–605. doi: 10.1161/CIRCULATIONAHA.106.621854 . PMID   16894049.
  14. ↑ Song, Xu; Bao, Mingmin; Li, Diandong; Li, Yong Ming (1999). "Advanced glycation in D-galactose induced mouse aging model". Mechanisms of Ageing and Development. 108 (3): 239–51. doi:10.1016/S0047-6374(99)00022-6. PMID   10405984. S2CID   8147556.
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