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Arbutin information


Not to be confused with the structurally similar stereoisomer alpha-arbutin.
Arbutin
Names
IUPAC name
4-Hydroxyphenyl-β-d-glucopyranoside
Systematic IUPAC name
(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
Other names
  • beta-Arbutin
  • β-Arbutin
  • Arbutoside
  • Hydroquinone β-d-glucopyranoside
  • 4-Hydroxyphenyl β-d-gluco-hexopyranoside
Identifiers
CAS Number
  • 497-76-7 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
 89673
ChEBI
  • CHEBI:18305 checkY
ChEMBL
  • ChEMBL232202 checkY
ChemSpider
  • 389765 checkY
DrugBank
  • DB11217
ECHA InfoCard 100.007.138 Edit this at Wikidata
EC Number
  • 207-850-3
KEGG
  • C06186 checkY
MeSH Arbutin
PubChem CID
  • 346
RTECS number
  • CE8663000
UNII
  • C5INA23HXF checkY
CompTox Dashboard (EPA)
  • DTXSID7040152 Edit this at Wikidata
InChI
  • InChI=1S/C12H16O7/c13-5-8-9(15)10(16)11(17)12(19-8)18-7-3-1-6(14)2-4-7/h1-4,8-17H,5H2/t8-,9-,10+,11-,12-/m1/s1 checkY
    Key: BJRNKVDFDLYUGJ-RMPHRYRLSA-N checkY
  • Key: BJRNKVDFDLYUGJ-RMPHRYRLBW
SMILES
  • C1=CC(=CC=C1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
Properties[2]
Chemical formula
 C12H16O7
Molar mass 272.25
Appearance Colorless to white solid powder
Melting point 197–201 °C (387–394 °F; 470–474 K)
Solubility in water
 5.0 g/100 mL
Solubility slightly soluble in ethyl ether, benzene and chloroform
Solubility in ethanol soluble
log P –1.35
Vapor pressure 2.3×10−12 mm Hg (25 °C)
Acidity (pKa) 10.10
UV-vis (λmax) 285 nm[1]
Pharmacology
ATC code
 D11 (WHO)
Routes of
administration
 Topically
Pharmacokinetics:
Bioavailability
 0.53% percutaneous absorption[3]
Legal status
  • US: Not FDA approved
  • EU: Unscheduled
Hazards[2]
Occupational safety and health (OHS/OSH):
Ingestion hazards
 Low level of toxicity
Eye hazards
 Irritation
Skin hazards
 Irritation
GHS labelling:
Pictograms
 GHS07: Exclamation mark
Signal word
 Warning
Hazard statements
 H315, H319, H335
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
1
0
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 9.8 g/kg (mouse, oral), 8.7 g/kg (rat, oral), 978 mg/kg (rat, mouse, dermal) (maximum practically applicable dosage)[2]
Safety data sheet (SDS) Sigma-Aldrich
Related compounds
Related compounds
    • α-Arbutin
    • γ-Arbutin
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

beta-Arbutin, also known as β-arbutin or by its International Nomenclature of Cosmetic Ingredients (INCI) name, arbutin, is a glycosylated derivative of hydroquinone. β-Arbutin is naturally present in the leaves and bark of a variety of plants, notably the bearberry plant, Arctostaphylos uva-ursi. Utilized as a biosynthetic active ingredient in topical treatments for skin lightening, β-arbutin is aimed at addressing hyperpigmentation issues. Its mechanism of action involves inhibiting the activity of tyrosinase, an essential enzyme for melanin synthesis in the human skin, thereby leading to a reduction in hyperpigmentation. It is important to distinguish β-arbutin from its structurally similar stereoisomer, α-arbutin, which exhibits similar effects in clinical applications.[3]

  1. ^ "SCCS (Scientific Committee on Consumer Safety), Opinion on the safety of alpha- (CAS No. 84380-018, EC No. 617-561-8) and beta-arbutin (CAS No. 497-76-7, EC No. 207-8503) in cosmetic products, preliminary version of 15-16 March 2022, final version of 31 January 2023, SCCS/1642/22" (PDF). European Commission. 2023-02-01. Retrieved 2023-03-07.
  2. ^ a b c Sccs; Degen, Gisela H. (2015). "Opinion of the Scientific Committee on Consumer Safety (SCCS) – Opinion on the safety of the use of β-arbutin in cosmetic products". Regulatory Toxicology and Pharmacology. 73 (3): 866–867. doi:10.1016/j.yrtph.2015.10.008.
  3. ^ a b Scientific Committee on Consumer Safety (SCCS) (1 February 2023). "Opinion on the safety of alpha- (CAS No. 84380-018, EC No. 617-561-8) and beta-arbutin (CAS No. 497-76-7, EC No. 207-8503) in cosmetic products, preliminary version of 15–16 March 2022, final version of 31 January 2023, SCCS/1642/22" (PDF). European Commission (Expert Opinion). Retrieved 7 March 2024.

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Arbutin

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beta-Arbutin, also known as β-arbutin or by its International Nomenclature of Cosmetic Ingredients (INCI) name, arbutin, is a glycosylated derivative of...

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Anal bleaching

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ingredients that are used in skin lightening cosmetics are arbutin and kojic acid. Arbutin, often also called bearberry, can be converted by the body...

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Bergenia crassifolia

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Laurian; Tamas, Mircea (2009). "Natural Resources Containing Arbutin. Determination of Arbutin in the Leaves of Bergenia crassifolia (L.) Fritsch. acclimated...

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Rhododendron ferrugineum

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in the Alps. Rhododendron ferrugineum is moderately toxic, containing arbutin, arecoline and rhodoxanthin, and can cause vomiting, and difficulties of...

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Glucoside

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example, in the flavonoids chemical family. Arbutin, which occurs in bearberry along with methyl arbutin, hydrolyses to hydroquinone and glucose. Pharmacologically...

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C12H16O7

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The molecular formula C12H16O7 may refer to: α-Arbutin β-Arbutin This set index page lists chemical structure articles associated with the same molecular...

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Bearberry

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acid, gallic acid, some essential oils and resin, hydroquinones (mainly arbutin, up to 17%), tannins (up to 15%), phenolic glycosides and flavonoids...

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Melasma

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involve inhibition of melanin synthesis pathway Kojic acid (2%) OTC Alpha Arbutin 2–5% OTC Flutamide (1%) Chemical peels Microdermabrasion to dermabrasion...

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Acne

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sunscreen can minimize such a risk. Whitening agents like azelaic acid, arbutin or else may be used to improve hyperpigmentation. Risk factors for the...

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Turnera diffusa

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aphrodisiaca. Damiana contains damianin; tetraphyllin B; gonzalitosin I; arbutin; tricosan-2-one; acacetin; p-cymene; β-sitosterol; 1,8-cineole; apigenin;...

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Kalmia latifolia

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horses, goats, cattle, deer, monkeys, and humans, due to grayanotoxin and arbutin. The green parts of the plant, flowers, twigs, and pollen are all toxic...

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Glycoside

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fragility. Here, the aglycone is a simple phenolic structure. An example is arbutin found in the Common Bearberry Arctostaphylos uva-ursi. It has a urinary...

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Ehretia tinifolia

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and leaves; These contain tannin, gallic acid resin, and a glucoside, arbutin, which has diuretic (facilitates urine) properties. It also manages to...

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List of poisonous plants

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Kalmia latifolia mountain laurel Ericaceae Contains andromedotoxin and arbutin. The green parts of the plant, flowers, twigs, and pollen are all toxic...

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Light skin in Japanese culture

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Welfare has recognized a combination of active ingredients. These are mainly arbutin and kojic acid. Other ingredients include vitamin C derivatives and tranexamic...

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Glossary of chemical formulae

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isoelemicin C12H16O3 oudenone C12H16O4 2,4,5-Trimethoxypropiophenone C12H16O7 arbutin 497-76-7 C12H17N5O4S thiamine nitrate C12H18N4O2 E1210 C12H18O propofol...

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Cosmetics

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acid. Hyperpigmentation treatment: Kojic acid soap, cream, or powder, and Arbutin (a b-D-glucopyranoside derivative of hydroquinone) serum or cream help...

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Adenostoma fasciculatum

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ferulic acid, syringic acid, vanillic acid, p-hydroxybenzoic acid and arbutin have been identified within the plant. Furthermore, umbelliferone and phlorizin...

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Pineapple

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acid, sinapic acid, coumaric acid, chlorogenic acid, epicatechin, and arbutin. Present in all parts of the pineapple plant, bromelain is a mixture of...

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Proteaceae

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(delphinidin and cyanidin), flavonols (kaempferol, quercetin and myricetin) and arbutin. Alkaloids are usually absent. Iridoids and ellagic acid are also absent...

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Taxifolin

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Also taxifolin inhibited the cellular melanogenesis as effectively as arbutin, one of the most widely used hypopigmenting agents in cosmetics. Taxifolin...

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Chronic bacterial prostatitis

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in combination with Serenoa repens extract, Lactobacillus Sporogens and Arbutin. Large prostatic stones was shown to be related with the presence of bacteria...

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List of compounds with carbon number 22

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C22H26N2O2 vinpocetine 42971-09-5 C22H26O3 resmethrin 10453-86-8 C22H26O12 arbutin pentaacetate 14698-56-7 C22H27NO phenazocine 127-35-5 C22H27NO2 amineptine...

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Natural skin care

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coffee berry, curcumin, green tea, pomegranate, licorice, paper mulberry, arbutin, and soy. "Many of these botanical sources offer biologically active components...

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Hydroquinone glucosyltransferase

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UDP-glucose:hydroquinone-O-beta-D-glucosyltransferase. Other names in common use include arbutin synthase, and hydroquinone:O-glucosyltransferase. Arend J, Warzecha H,...

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Kalmia polifolia

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the active compounds within Kalmia polifolia include andromedotoxin and arbutin. These compounds cause a slowing of pulse, a lowering of blood pressure...

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Hanseniaspora gamundiae

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maltose, or lactose. The yeast can assimilate glucose, sucrose, cellobiose, arbutin, and salicin. It has a positive growth rate at 30°C, but there is no growth...

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