Showing Compound Arbutin (FDB001221)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:53 UTC

Update date

2020-02-24 19:10:21 UTC

Primary ID

FDB001221

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Arbutin

Description

Arbutin, also known as arbutoside or beta-arbutin, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Arbutin is an extremely weak basic (essentially neutral) compound (based on its pKa). Arbutin is a bitter tasting compound. Arbutin is found, on average, in the highest concentration within a few different foods, such as bilberries, quinces, and pears. Arbutin has also been detected, but not quantified in, several different foods, such as sweet marjorams, apples, pomes, yali pears, and milk (cow). This could make arbutin a potential biomarker for the consumption of these foods.

CAS Number

497-76-7

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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Synonym	Source
4-Hydroxyphenyl b-D-glucopyranoside, 9ci, 8ci	HMDB
4-Hydroxyphenyl b-D-glucopyranoside, 9CI, 8CI	db_source
4-Hydroxyphenyl beta-D-glucopyranoside	HMDB
4-hydroxyphenyl beta-D-glucopyranoside	biospider
4-Hydroxyphenyl-beta-D-glucopyranoside	HMDB
Arbutinum	HMDB
Arbutoside	HMDB
beta -D-Glucopyranoside, 4-hydroxyphenyl	HMDB
beta-Arbutin	HMDB
Beta-arbutin	biospider

Showing 1 to 10 of 33 entries

Predicted Properties

Property	Value	Source
Water Solubility	39.1 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-0.9	ChemAxon
logS	-0.84	ALOGPS
pKa (Strongest Acidic)	9.82	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	119.61 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	62.16 m³·mol⁻¹	ChemAxon
Polarizability	25.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C12H16O7

IUPAC name

2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol

InChI Identifier

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

InChI Key

BJRNKVDFDLYUGJ-UHFFFAOYSA-N

Isomeric SMILES

OCC1OC(OC2=CC=C(O)C=C2)C(O)C(O)C1O

Average Molecular Weight

272.2512

Monoisotopic Molecular Weight

272.089602866

Classification

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
4-alkoxyphenol
Phenoxy compound
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Oxane
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Primary alcohol
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

a small molecule (HYDROQUINONE-O-BETA-D-GLUCOPYRANOSIDE )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	-1.35	HANSCH,C ET AL. (1995)
Experimental pKa	10
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 52.94%; H 5.92%; O 41.14%	DFC
Melting Point	Mp 142-143°	DFC
Optical Rotation	[a]18D -60.34 (H2O)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Arbutin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0w29-5950000000-b06dd9542fa7bbd667f2	Spectrum
Predicted GC-MS	Arbutin, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-2201239000-2f42b1022552b40a482e	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03k9-0970000000-7f1103faf15e6a906252	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-f96f8a574fa0e00ad323	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9800000000-5ea8ff882118ae29ef23	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05fr-1790000000-08eaec414aecf42a9f90	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1910000000-51e3a547305d55828467	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-4900000000-481f6d878e6db1bc8f7c	2015-04-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C06186

Pubchem Compound ID

440936

Pubchem Substance ID

Not Available

ChEBI ID

18305

Phenol-Explorer ID

659

DrugBank ID

Not Available

HMDB ID

HMDB29943

CRC / DFC (Dictionary of Food Compounds) ID

BWQ88-O:BWQ88-O

EAFUS ID

Not Available

Dr. Duke ID

ARBUTIN

BIGG ID

Not Available

KNApSAcK ID

C00002638

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Arbutin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Asian pear	Expected but not quantified	Not Available	18778075
Milk (Cow)	Expected but not quantified	Not Available	23438684
Yali pear	Expected but not quantified	Not Available	18778075
Bilberry	1500.000 - 1500.000	1500.000	DUKE
Lingonberry	Expected but not quantified	Not Available	KNAPSACK
Pear	0.000 - 1.398 mg/100 g	0.13133 mg/100 g	PHENOL EXPLORER, DUKE, KNAPSACK, 18778075, A. Escarpa and M. C. Gonzalez. Evaluation of High-Performance Liquid Chromatography for Determination of Phenolic Compounds in Pear Horticultural Cultivars. Chromatographia Vol. 51, No. 1/2, January 2000, 37-43, PHYTOHUB
Quince	2.689 - 2.689 mg/100 g	2.689 mg/100 g	PHENOL EXPLORER
Sweet marjoram	Expected but not quantified	Not Available	DUKE, KNAPSACK, PHYTOHUB
Wheat	Expected but not quantified	Not Available	PHYTOHUB
Wheat bread	Expected but not quantified	Not Available	PHYTOHUB

Showing 1 to 10 of 10 entries

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
allelochemic			DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti edemic			DUKE
anti melanogenic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti streptococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti tussive	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
artemicide			DUKE
candidicide			DUKE
diuretic	35498	An agent that promotes the excretion of urine through its effects on kidney function.	DUKE