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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
Introduction: Diuretic and anti-infective drugs of urinary system. Color photographic developing stabilizer. Whitening, anti-freckle, hair care in cosmetics.
1. Names and Identifiers
1.1 Name
Arbutin
1.2 Synonyms

4-Hydroxyphenyl &beta 4-hydroxyphenyl-beta-d-glucopyranosid 4-HYDROXYPHENYL-BETA-D-GLUCOPYRANOSIDE Arbutin (natural) arbutin,beta-arbutin beta-arbutin -D-Glucopyranoside -D-glucoside Hydroquinone-&beta Hydroquinone-glucose

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 InChkey
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
3.1 Density
1.556g/cm3
3.2 Melting Point
195-198°C
3.3 Boiling Point
561.6ºC at 760 mmHg
3.4 Vapour
1.9E-13mmHg at 25°C
3.5 Refractive Index
-65.5 ° (C=4, H2O)
3.6 Flash Point
293.4ºC
3.7 Alpha
-64 o (C=3)
3.8 Appearance
white powder
3.9 Chemical Properties
Crystalline powder
3.10 Color/Form
Powder
3.11 pKa
10.10±0.15(Predicted)
3.12 Solubility
H2O: 50?mg/mL hot, clear
3.13 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)
3.14 Stability
Stable. Hygroscopic - store under dry nitrogen.
3.15 Water Solubility
50mg/mL in water
3. Use and Manufacturing
4.1 Definition
ChEBI: A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.
4.2 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
4.3 Methods of Manufacturing
Pure arbutin; can be prepared synthetically from acetobromoglucose and hydroquinone; in the presence of alkali
4.4 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
4.5 Storage
Hygroscopic. Air Sensitive. Ambient temperatures.
4.6 Usage
Diuretic and anti-infective drugs of urinary system. Color photographic developing stabilizer. Whitening, anti-freckle, hair care in cosmetics.
4. Safety and Handling
5.1 Hazard Codes
Xn
5.2 Risk Statements
R20/21/22
5.3 Safety Statements
S22; S24/25; S36; S26
5.4 Transport
OTH
5.5 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.
5.6 Octanol/Water Partition Coefficient
log Kow = -1.35
5.7 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

5.8 Sensitive
Hygroscopic
5.9 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.?

5.10 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)
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. Computational chemical data
  • Molecular Weight:272.25100g/mol
  • Molecular Formula:C12H16O7
  • Compound Is Canonicalized:True
  • XLogP3-AA:
  • 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
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