CAS 122-48-5|zingerone|Vanillylacetone|4-(4-hydroxy-3-methoxyphenyl)butan-2-one|ZINGERONE|4-(4-hydroxy-3-methoxyphenyl)butan-2-one|Zingerone|Vanillylacetone|4-(4-Hydroxy-3-methoxyphenyl)-2-butanone|...

General Information

Structure

Molecular Formula

C₁₁H₁₄O₃

Molecular Mass

194.22706

Exact Mass

194.09429431

Charge

InChI

InChI=1S/C11H14O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-7,13H,3-4H2,1-2H3

InChIKey

OJYLAHXKWMRDGS-UHFFFAOYSA-N

Canonic Smiles

COc1cc(CCC(=O)C)ccc1O

Isomeric Smiles

c1c(c(cc(c1)CCC(=O)C)OC)O

Calculated Properties

JChem

LogD (pH = 7.4)

1.92

LogD (pH = 5.5)

1.92

Log P

1.92

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

9.95

Polar Surface Area

46.53

Polarizability

20.93

Molar Refractivity

53.96

LOG S

-1.25

Data Source

Names and Identifiers

IUPAC Traditional name

zingerone

IUPAC name

4-(4-hydroxy-3-methoxyphenyl)butan-2-one

Synonyms

VanillylacetoneZINGERONE4-(4-hydroxy-3-methoxyphenyl)butan-2-one4-(4-羟基-3-甲氧基苯)-2-丁酮4-(4-Hydroxy-3-methoxyphenyl)-2-butanoneVanillylacetoneZingerone姜酮姜油酮Vanillylacetone[0]-Paradol4-(3-methoxy-4-hydroxyphenyl)butan-2-one3-Methoxy-4-hydroxybenzylacetone4-Hydroxy-3-methoxybenzylacetone2-(4-Hydroxy-3-methoxyphenyl)ethyl methyl ketonezingeroneZingheroneGingerone4-(4-Hydroxy-3-methoxyphenyl)-2-butanoneVanillylacetone4-(3-Methoxy-4-hydroxyphenyl)-2-butanone(0)-ParadolZingiberonevanillylacetone(4-Hydroxy-3-methoxyphenyl)ethyl methyl ketone

Names and Identifiers

Registration numbers

EC Number

204-548-3

MDL Number

MFCD00048232

PubChem SID

24901474162037915160645760

Flavis Number

7.005

CAS Number

122-48-5

FEMA ID

3124

Council of Europe Number

CHEMBL

PubChem CID

Wikipedia Title

CHEBI ID

Unique Ingredient Identifier

4MMW850892

Chemspider ID

28952

Patent number

EP1336602US6432441US6500797DE102009055915WO2011063865US5035882WO2011063864US5908770US2002051800US2003068276EP2327393WO2011063863US6306429

PubMed Citation Links

2155195518670185225960782060637920799069202112361945973622173270194639662232963018472135193671222071343221802408219293292176964221335001

BRENDA Database

1.11.1.131.1.3.B53.4.24.261.1.1.212.1.1.1462.4.1.4

MetaboLights Database

MTBLS392MTBLS2825MTBLS4099MTBLS2330MTBLS2358MTBLS2878MTBLS4967MTBLS1918MTBLS2096

SureChEMBL Database

SCHEMBL119051

BRENDA Ligand Database

Reaxys Registry

NMRShiftDB Database

Beilstein Number

BKMS React Database

CompTox Database

ACToR Database

HMDB Database

KEGG ID

BindingDB Database

Registration numbers

Properties

Pharmacology Properties

Allergens

no known allergens

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Selleck Chemicals

S2371

Research Area: Endocrinology
Biological Activity:
Vanillylacetone is similar in chemical structure to other flavor chemicals such as vanillin and eugenol. It is used as a flavor additive in spice oils and in perfumery to introduce spicy aromas.Fresh ginger does not contain vanillylacetone; cooking the ginger transforms gingerol, which is present, into vanillylacetone through a retro-aldol reaction. Vanillylacetone is likely the active constituent responsible for the antidiarrheal efficacy of ginger. [1]

MP Biomedicals

05219828

MP Biomedicals Rare Chemical collection

Wikipedia

Zingerone

Sigma Aldrich

W312401

Biochem/physiol Actions
Taste at 20 ppm in 5%
Other Notes
Natural occurrence: Cranberry and ginger.
Packaging
1 kg in poly bottle
1 sample in glass bottle
100, 250 g in poly bottle

ChEBI

CHEBI:68657

A methyl ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at positions 3 and 4 by methoxy and hydroxy groups respectively. The major pungent component in ginger.

Molecule Details

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Vanillylacetone

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

zingerone

IUPAC name

4-(4-hydroxy-3-methoxyphenyl)butan-2-one

Synonyms

Registration numbers

EC Number

204-548-3

MDL Number

MFCD00048232

PubChem SID

24901474162037915160645760

Flavis Number

7.005

CAS Number

122-48-5

FEMA ID

3124

Council of Europe Number

CHEMBL

PubChem CID

Wikipedia Title

CHEBI ID

Unique Ingredient Identifier

4MMW850892

Chemspider ID

28952

Patent number

EP1336602US6432441US6500797DE102009055915WO2011063865US5035882WO2011063864US5908770US2002051800US2003068276EP2327393WO2011063863US6306429

PubMed Citation Links

2155195518670185225960782060637920799069202112361945973622173270194639662232963018472135193671222071343221802408219293292176964221335001

BRENDA Database

1.11.1.131.1.3.B53.4.24.261.1.1.212.1.1.1462.4.1.4

MetaboLights Database

MTBLS392MTBLS2825MTBLS4099MTBLS2330MTBLS2358MTBLS2878MTBLS4967MTBLS1918MTBLS2096

SureChEMBL Database

SCHEMBL119051

BRENDA Ligand Database

Reaxys Registry

NMRShiftDB Database

Beilstein Number

BKMS React Database

CompTox Database

ACToR Database

HMDB Database

KEGG ID

BindingDB Database

Molecule Details

S2371

MP Biomedicals Rare Chemical collection

Wikipedia

Zingerone

Sigma Aldrich

W312401

Biochem/physiol Actions
Taste at 20 ppm in 5%
Other Notes
Natural occurrence: Cranberry and ginger.
Packaging
1 kg in poly bottle
1 sample in glass bottle
100, 250 g in poly bottle

ChEBI

CHEBI:68657

A methyl ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at positions 3 and 4 by methoxy and hydroxy groups respectively. The major pungent component in ginger.

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Vanillylacetone

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

Allergens

no known allergens

Molecule

ID:72995