AFCDB: Vanilloside (FDB000840)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:44 UTC

Update date

2020-02-24 19:10:15 UTC

Primary ID

FDB000840

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Vanilloside

Description

Vanilloside 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. Vanilloside is a very mild, bitter, and vanilla tasting compound. Vanilloside has been detected, but not quantified in, a few different foods, such as breakfast cereal, cereals and cereal products, and oats (Avena sativa). This could make vanilloside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Vanilloside.

CAS Number

494-08-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	10.9 g/L	ALOGPS
logP	-0.95	ALOGPS
logP	-1	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	73.23 m³·mol⁻¹	ChemAxon
Polarizability	30.06 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-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzaldehyde

InChI Identifier

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

InChI Key

LPRNQMUKVDHCFX-UHFFFAOYSA-N

Isomeric SMILES

COC1=C(OC2OC(CO)C(O)C(O)C2O)C=CC(C=O)=C1

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
Hexose monosaccharide
O-glycosyl compound
Phenoxy compound
Anisole
Benzaldehyde
Methoxybenzene
Benzoyl
Phenol ether
Alkyl aryl ether
Aryl-aldehyde
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Ether
Organoheterocyclic compound
Acetal
Oxacycle
Polyol
Aldehyde
Alcohol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Poaceae

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 53.50%; H 5.77%; O 40.73%	DFC
Melting Point	Mp 188-192°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]20D -88.7 (H2O)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Vanilloside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0kgk-9480000000-c158d3c2c5d79698074f	Spectrum
Predicted GC-MS	Vanilloside, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-1211190000-856afe3b8b9ed78fa842	Spectrum
Predicted GC-MS	Vanilloside, 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	splash10-0uxr-0933000000-452354c3868de898b5c4	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-240644336a6730864119	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f79-2900000000-d838e0093c0048ed3a85	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ik9-1938000000-1c0ed402c606cd2029f0	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udr-1920000000-a313f0fd42a192b9e740	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f79-4900000000-11a9d143106555fac0db	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0w2i-0904000000-3f236699a279a1ea8744	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0k9i-3920000000-49daaa8810f4d82a28f7	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06ri-3902000000-d38a9afed48f9df0081f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-0759000000-e167034d7b96df80df5d	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ums-0910000000-ff7902020073bfe3e0f4	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfr-3910000000-ee55c7697274b5fc674c	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

2882053

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

3648225

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB29664

CRC / DFC (Dictionary of Food Compounds) ID

HCW75-Q:BJR58-X

EAFUS ID

Not Available

Dr. Duke ID

GLUCOVANILLIN|AVENEIN

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

rw1407591

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

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
very mild	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
vanilla	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755

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).

Vanilloside (FDB000840)

Structure for FDB000840 (Vanilloside)