Guidechem | China Chemical Manufacturers,suppliers,B2B Marketplace
Encyclop..
  • Products
  • Encyclopedia
  • Buy offers
  • Suppliers
Home> Encyclopedia >Urinary System Agents>Cosmetic Raw Materials>Pharmaceutical Intermediates
Arbutin structure
Arbutin structure

Arbutin

Iupac Name:(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
CAS No.: 497-76-7
Molecular Weight:272.25100
Modify Date.: 2022-11-01 01:52
Introduction:

Arbutin (C₁₂H₁₆O₇) is an organic compound. It is a colorless to white crystalline powder or solid with a faint, slightly sweet odor. The compound is soluble in water and alcohol and is often used in its purified form for cosmetic and pharmaceutical applications. Arbutin is a glycoside, consisting of hydroquinone and glucose, and is primarily known for its skin-lightening properties due to its ability to inhibit melanin production. It is commonly found in several plant species, including bearberry, cranberry, and blueberry, which are its primary natural sources.

Arbutin was first isolated from the leaves of the bearberry plant (Arctostaphylos uva-ursi) in the 19th century. Its use in traditional medicine has long been linked to its mild diuretic and urinary tract health benefits. In the 20th century, researchers discovered that Arbutin possesses the ability to inhibit tyrosinase, the enzyme responsible for melanin production, thus making it a popular ingredient in skin-whitening products. Today, Arbutin is widely used in cosmetics and dermatology to treat hyperpigmentation, age spots, and other skin discolorations. It is also found in dietary supplements targeting urinary tract health. Arbutin is usually synthesized through the glycosylation of hydroquinone, although it can also be extracted from its natural sources.

Arbutin is generally regarded as safe for topical use, but excessive oral consumption of high doses can lead to potential health risks. Large amounts of Arbutin are metabolized into hydroquinone, which can cause toxicity in the liver and kidneys if accumulated in the body. Hydroquinone is classified as a potential human carcinogen by some health authorities, and thus, excessive exposure may increase the risk of cancer and cause damage to tissues. However, when used appropriately, especially in skincare formulations, Arbutin is considered safe. It is important to note that Arbutin is contraindicated in pregnant or breastfeeding women due to its potential to release hydroquinone. The compound should be stored in a cool, dry, and well-ventilated area, away from light and moisture, to preserve its stability. The recommended storage temperature is below 25°C, and it should be kept in tightly sealed containers to avoid degradation.

View more+
1. Names and Identifiers
1.1 Name
Arbutin
1.2 Synonyms

(2R,3S,4S,5R,6S)-2-(Hydroxyméthyl)-6-(4-hydroxyphénoxy)tétrahydro-2H-pyran-3,4,5-triol (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(4-hydroxyphenoxy)tetrahydro-2H-pyran-3,4,5-triol 4-Hydroxyphenyl Beta-D-Glucopyranoside 4-Hydroxyphenyl β-D-galactopyranoside 4-Hydroxyphenyl Β-D-glucopyranoside 4-Hydroxyphenyl-b-D-glucopyranoside 4-Hydroxyphenyl-Β-D-glucopyranoside 4-Hydroxyphenyl-Β-D-glucopyranosidep 4-Hydroxyphenyl-Β-glucopyranoside 5-17-07-00110 Arbutin ARBUTOSIDE Arbutosie b-Arbutin EINECS 207-850-3 Ericolin) hydroquinone O-beta-D-glucopyranoside hydroquinone O-Β-D-glucopyranoside Hydroquinone-b-D-glucopyranoside Hydroquinone-Β-D-glucopyranoside HydroquinoneΒ-D-glucopyranoside Hydroquinone-Β-D-glucoside MFCD00016915 P-ARBUTIN p-Hydroxyphenyl Β-D-glucopyranoside Uresol URSIN UVASOL β-D-Galactopyranoside, 4-hydroxyphenyl Β-D-Glucopyranoside, 4-hydroxyphenyl

View all
1.3 CAS No.
497-76-7
1.4 CID
440936
1.5 EINECS(EC#)
207-850-3
1.6 Molecular Formula
C12H16O7 (isomer)
1.7 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
1.8 InChIkey
BJRNKVDFDLYUGJ-RMPHRYRLSA-N
1.9 Canonical Smiles
C1=CC(=CC=C1O)OC2C(C(C(C(O2)CO)O)O)O
1.10 Isomers Smiles
C1=CC(=CC=C1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
2. Properties
2.1 Density
1.556g/cm3
2.1 Melting point
195-198°C
2.1 Boiling point
561.6ºC at 760 mmHg
2.1 Refractive index
-65.5 ° (C=4, H2O)
2.1 Flash Point
293.4ºC
2.1 Precise Quality
272.09000
2.1 PSA
119.61000
2.1 logP
-1.42910
2.1 Solubility
H2O: 50?mg/mL hot, clear
2.2 Appearance
white powder
2.3 Storage
Hygroscopic. Air Sensitive. Ambient temperatures.
2.4 Chemical Properties
Crystalline powder
2.5 Color/Form
Powder
2.6 pKa
10.10±0.15(Predicted)
2.7 Water Solubility
10-15 g/100 mL at 20 oC
2.8 Spectral Properties
Specific optical rotation: -60.3 deg at 20 deg C/D (in water)
Specific optical rotation: -64 deg at 25 deg C/D (3% water)
IR: 18673 (Sadtler Research Laboratories IR grating collection)
UV: 4704 (Sadtler Research Laboratories spectral collection)
1H NMR: 4444 (Sadtler Research Laboratories spectral collection)
2.9 Stability
Stable. Hygroscopic - store under dry nitrogen.
3. Use and Manufacturing
3.1 Definition
ChEBI: A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.
3.2 GHS Classification
Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 32 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 30 of 32 companies. For more detailed information, please visit ECHA C&L website

Of the 1 notification(s) provided by 2 of 32 companies with hazard statement code(s):

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501
View all
3.3 Methods of Manufacturing
Pure arbutin; can be prepared synthetically from acetobromoglucose and hydroquinone; in the presence of alkali
3.4 Purification Methods
The glycoside from Protea exima is purified by recrystallisation from H2O or moist EtOAc (as monohydrate), after chromatography through silica Gel using EtOAc/MeOH. Crystallisation from EtOH/CHCl3 gives crystals m 199-200o with intermediate melting at 164o and resolidifying. The pentaacetate crystallises from EtOH in fine needles with m 145-146o, [] D 20 -28.2o (c 2, Me2CO). [Robinson & Waters J Chem Soc 2729 1930, IR, NMR, MS: Perold et al. J Chem Soc, Perkin Trans 1 239 1979, Beilstein 17/7 V 110.] ArbutinSupplier
3.5 Usage
Diuretic and anti-infective drugs of urinary system. Color photographic developing stabilizer. Whitening, anti-freckle, hair care in cosmetics.
4. Safety and Handling
4.1 Hazard Codes
Xn
4.1 Risk Statements
R20/21/22
4.1 Safety Statements
S22; S24/25; S36; S26
4.1 Octanol/Water Partition Coefficient
log Kow = -1.35
4.2 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
4.3 RIDADR
OTH
4.3 WGK Germany
3
4.3 RTECS
CE8863000
4.3 Safety

An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes:?HarmfulXn
Risk Statements: 20/21/22-36/37/38
20/ 21/22(Harmful by inhalation,in contact with skin and if swallowed)
36/37/38 (Irritating to the eyes piratory system and skin)
Safety Statements: 22-24/25-36-26
22(Do not breathe dust)
24/25(Avoid contact with skin and eyes)
36(Wear suitable protective clothing)
26 (In case of contact with eyes,rinse immediately with plenty of water and seek medical advice)
WGK Germany: 3
RTECS: CE8863000
F: 3-10-23

4.4 Sensitive
Hygroscopic
4.5 Specification

? Arbutin , with CAS number of 497-76-7, can be called (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol ; Arbutoside ; Hydroquinone-O-beta-D-glucopyranoside ; Hydroquinone .beta.-D-glucopyranoside ; p-Hydroxyphenyl beta-D-glucoside ; 4-Hydroxyphenyl-beta-D-glucopyranoside .?Arbutin (CAS NO.497-76-7) should be stored in a cool, dry place with?a tightly closed container.?

4.6 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :
CE8863000
CHEMICAL NAME :
Arbutin
CAS REGISTRY NUMBER :
497-76-7
BEILSTEIN REFERENCE NO. :
0089673
LAST UPDATED :
199709
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C12-H16-O7
MOLECULAR WEIGHT :
272.28

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
13600 mg/kg
SEX/DURATION :
female 14 day(s) pre-mating female 20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 19,282,1988 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X1290 No. of Facilities: 68 (estimated) No. of Industries: 1 No. of Occupations: 3 No. of Employees: 995 (estimated) No. of Female Employees: 745 (estimated)
View all
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)

none

Precautionary statement(s)
Prevention

none

Response

none

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 Usage
Arbutin, a glycosylated hydroquinone, is used in studies on melanin biosynthesis and as an inhibitor to identify, differentiate and characterize tyrosinase(s). Also used in sed as a skin-lightening agent in cosmetic products.
10. Computational chemical data
  • Molecular Weight: 272.25100g/mol
  • Molecular Formula: C12H16O7
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 272.08960285
  • Monoisotopic Mass: 272.08960285
  • Complexity: 279
  • Rotatable Bond Count: 3
  • Hydrogen Bond Donor Count: 5
  • Hydrogen Bond Acceptor Count: 7
  • Topological Polar Surface Area: 120
  • Heavy Atom Count: 19
  • Defined Atom Stereocenter Count: 5
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADceBwOAAAAAAAAAAAAAAAAAAAAAAAAAA0QAAAAAAAAAABAAAAGgAACAAACBSwkAMwDoAABgCAACBCAAACCAAgIAAIiAAGCIgdNiKGMRqieCClwBEPuAfAYAwAAQAAAAAAAAACAAAAAAAAAAAAAAAAAA==
11. Question & Answer
12. Recommended Suppliers
Global500SuppliersView all >>
  • Products:API',s intermediates,fine chemicals and plant extracts.
  • Tel:86-917-3909592
  • Email:gksales1@gk-bio.com
Arbutin
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 0 USD/kg
  • Time: 2024/12/30
Inquire
  • Products:Plastic particles, chemical products
  • Tel:+86-22-13149459979
  • Email:jennifer@furuntongda.com
High purity beta-Arbutin CAS 497-76-7 supplied by reliable manufacturer Superior Quality
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 20 USD/kg
  • Time: 2025/01/02
Inquire
  • Products:carbomer940,uv627
  • Tel:86-311-13315458396
  • Email:may@hbmojin.com
High Quality 99% Arbutin CAS 497-76-7 with Best Price
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 1 USD/kg
  • Time: 2025/01/02
Inquire
  • Products:Division I, the main production Lead acetate phenylacetamide Cyromazine quality is very good!
  • Tel:86-185-31123677
  • Email:xing@yan-xi.com
Arbutin
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 1 USD/kilogram
  • Time: 2025/01/02
Inquire
  • Products:API & Intermediates, Food Addititives,Fine Chemicals. Biochemical & Reagent
  • Tel:86-27-59207850
  • Email:info@fortunachem.com
High quality beta-Arbutin CAS 497-76-7 supplied by reliable manufacturer
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 300 USD/kilogram
  • Time: 2024/08/08
Inquire
13. Realated Product Infomation