Showing Compound 6-O-Acetylarbutin (FDB012309)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:06 UTC

Update date

2019-11-26 03:06:33 UTC

Primary ID

FDB012309

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

6-O-Acetylarbutin

Description

6-O-Acetylarbutin 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. 6-O-Acetylarbutin has been detected, but not quantified in, several different foods, such as breakfast cereal, cereals and cereal products, fruits, pears (Pyrus communis), and pomes. This could make 6-O-acetylarbutin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 6-O-Acetylarbutin.

CAS Number

10338-88-2

Structure

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

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	12.7 g/L	ALOGPS
logP	-0.59	ALOGPS
logP	-0.46	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	9.82	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	71.32 m³·mol⁻¹	ChemAxon
Polarizability	30.14 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

C14H18O8

IUPAC name

[3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl acetate

InChI Identifier

InChI=1S/C14H18O8/c1-7(15)20-6-10-11(17)12(18)13(19)14(22-10)21-9-4-2-8(16)3-5-9/h2-5,10-14,16-19H,6H2,1H3

InChI Key

XABUTYXAHYMCDK-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

314.2879

Monoisotopic Molecular Weight

314.100167552

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
O-glycosyl compound
4-alkoxyphenol
Phenoxy compound
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Polyol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Poaceae

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

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	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 53.50%; H 5.77%; O 40.73%	DFC
Melting Point	Mp 214-216°	DFC
Optical Rotation	[a]23D -58.8 (c, 2.0 in H2O)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	6-O-Acetylarbutin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4m-6790000000-32b670fca7a465299288	Spectrum
Predicted GC-MS	6-O-Acetylarbutin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-2100190000-d7b2bb46eee30eca53fa	Spectrum
Predicted GC-MS	6-O-Acetylarbutin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-O-Acetylarbutin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-1953000000-b13e3ee13b222867f4b2	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1910000000-d7e4ebc08c026cd610c3	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9800000000-9c41664b859673bdf919	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9624000000-96fecb06a2bccdd4998a	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9810000000-a99cc3a2d6571c2a77ad	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9800000000-010a34b1bab3b6a46a06	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0933000000-e7af6c67b8a31ec1189b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-3930000000-7b7648a275ba1f4b190d	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dj-8900000000-9323f442de24ae44d4c5	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0901000000-e7ab68917bacf62a3764	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-5921000000-f52ade01f22408b2c3e7	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9700000000-7ab82dafbea7e6ccf4ad	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

13277076

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

5315513

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB34060

CRC / DFC (Dictionary of Food Compounds) ID

BWQ88-O:HFV90-H

EAFUS ID

Not Available

Dr. Duke ID

PYROSIDE|6-O-ACETYLARBUTIN

BIGG ID

Not Available

KNApSAcK ID

Not Available

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

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Search:

Food	Content Range	Average	Reference

Breakfast cereal	Expected but not quantified	Not Available	DFC CODES
Pear	Expected but not quantified	Not Available	DUKE

Showing 1 to 2 of 2 entries

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Showing Compound 6-O-Acetylarbutin (FDB012309)

Structure for FDB012309 (6-O-Acetylarbutin)