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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:40 UTC

Update Date

2023-02-21 17:22:25 UTC

HMDB ID

HMDB0032591

Secondary Accession Numbers

HMDB32591

Metabolite Identification

Common Name

Dehydrozingerone

Description

Dehydrozingerone, also known as vanillidene acetone or MMHSK, belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. Dehydrozingerone is a sweet, balsam, and creamy tasting compound. Based on a literature review very few articles have been published on Dehydrozingerone.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 05061306352D          

 14 14  0  0  0  0            999 V2000
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
  8  1  1  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
  9  5  1  0  0  0  0
  9  7  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11 10  2  0  0  0  0
 12  8  2  0  0  0  0
 13 10  1  0  0  0  0
 14  2  1  0  0  0  0
 14 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032591

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(\C=C/C(C)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h3-7,13H,1-2H3/b4-3-

> <INCHI_KEY>
AFWKBSMFXWNGRE-ARJAWSKDSA-N

> <FORMULA>
C11H12O3

> <MOLECULAR_WEIGHT>
192.2112

> <EXACT_MASS>
192.07864425

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
19.940533748476998

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3Z)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
2.004475195333333

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.685292811017217

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.511486304450656

> <JCHEM_PKA_STRONGEST_BASIC>
-4.528898028268719

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
55.05510000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3Z)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   14                                                            
CONECT    3    4    8                                                       
CONECT    4    3    9                                                       
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    9   11                                                       
CONECT    8    1    3   12                                                  
CONECT    9    4    5    7                                                  
CONECT   10    6   11   13                                                  
CONECT   11    7   10   14                                                  
CONECT   12    8                                                            
CONECT   13   10                                                            
CONECT   14    2   11                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0032591
HETATM    1  C1  UNL     1       3.708   1.744   0.352  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.524   0.403  -0.069  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.255  -0.177  -0.079  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.144   0.504   0.308  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.153  -0.057   0.308  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.179   0.759   0.864  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.410   0.807   0.477  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.006   0.091  -0.579  1.00  0.00           C  
HETATM    9  C8  UNL     1      -4.502   0.281  -0.785  1.00  0.00           C  
HETATM   10  O2  UNL     1      -2.500  -0.682  -1.383  1.00  0.00           O  
HETATM   11  C9  UNL     1      -0.205  -1.353  -0.113  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.940  -2.056  -0.514  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.186  -1.483  -0.505  1.00  0.00           C  
HETATM   14  O3  UNL     1       3.316  -2.196  -0.908  1.00  0.00           O  
HETATM   15  H1  UNL     1       4.776   1.962   0.532  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.301   2.424  -0.421  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.144   1.854   1.322  1.00  0.00           H  
HETATM   18  H4  UNL     1       1.255   1.522   0.631  1.00  0.00           H  
HETATM   19  H5  UNL     1      -0.906   1.441   1.742  1.00  0.00           H  
HETATM   20  H6  UNL     1      -3.102   1.513   1.056  1.00  0.00           H  
HETATM   21  H7  UNL     1      -4.976   0.674   0.122  1.00  0.00           H  
HETATM   22  H8  UNL     1      -4.952  -0.713  -0.983  1.00  0.00           H  
HETATM   23  H9  UNL     1      -4.654   0.903  -1.685  1.00  0.00           H  
HETATM   24  H10 UNL     1      -1.097  -1.946  -0.095  1.00  0.00           H  
HETATM   25  H11 UNL     1       0.873  -3.083  -0.847  1.00  0.00           H  
HETATM   26  H12 UNL     1       3.219  -3.137  -1.207  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   18
CONECT    5    6   11   11
CONECT    6    7    7   19
CONECT    7    8   20
CONECT    8    9   10   10
CONECT    9   21   22   23
CONECT   11   12   24
CONECT   12   13   13   25
CONECT   13   14
CONECT   14   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Vanillidene acetone	MeSH
4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one	MeSH
Dehydrozingerol	MeSH
Methyl-3-methoxy-4-hydroxystyryl ketone, (e)-iosmer	MeSH
4-Hydroxy-3-methoxybenzalacetone	MeSH
MMHSK	MeSH
Methyl-3-methoxy-4-hydroxystyryl ketone	MeSH
3-Methoxy-4-hydroxybenzalacetone	HMDB
4-Hydroxy-3-methoxybenzylideneacetone	HMDB
4-Hydroxy-3-methoxystyryl methyl ketone	HMDB
dehydro-[0]-Paradol	HMDB
FEMA 3738	HMDB
Feruloylmethane	HMDB
Methyl-3-methoxy-4-hydroxy styryl ketone	HMDB
MHSK	HMDB
Vanillalacetone	HMDB
Vanillylidenacetone	HMDB
Vanillylidene acetone	HMDB
Vanylidenacetone	HMDB
[0]-Dehydroparadol	HMDB
Dehydrozingerone	MeSH

Chemical Formula

C₁₁H₁₂O₃

Average Molecular Weight

192.2112

Monoisotopic Molecular Weight

192.07864425

IUPAC Name

(3Z)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one

Traditional Name

(3Z)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one

CAS Registry Number

1080-12-2

SMILES

COC1=C(O)C=CC(\C=C/C(C)=O)=C1

InChI Identifier

InChI=1S/C11H12O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h3-7,13H,1-2H3/b4-3-

InChI Key

AFWKBSMFXWNGRE-ARJAWSKDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids and derivatives

Alternative Parents

Substituents

Hydroxycinnamic acid or derivatives
Methoxyphenol
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Anisole
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Enone
Alpha,beta-unsaturated ketone
Acryloyl-group
Ketone
Ether
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032591)
Cytoplasm (HMDB: HMDB0032591)

Source

Endogenous

Endogenous (HMDB: HMDB0032591)

Plant

Plant (HMDB: HMDB0032591)

Exogenous

Food

Food (HMDB: HMDB0032591)

Exogenous (HMDB: HMDB0032591)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0032591)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	129 - 130 °C	Not Available
Boiling Point	344.00 to 345.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	3163 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.401 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.55 g/L	ALOGPS
logP	2.17	ALOGPS
logP	2	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	9.51	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	55.06 m³·mol⁻¹	ChemAxon
Polarizability	19.94 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	148.063	30932474
DeepCCS	[M-H]-	145.705	30932474
DeepCCS	[M-2H]-	179.936	30932474
DeepCCS	[M+Na]+	154.617	30932474
AllCCS	[M+H]+	141.7	32859911
AllCCS	[M+H-H2O]+	137.4	32859911
AllCCS	[M+NH4]+	145.7	32859911
AllCCS	[M+Na]+	146.8	32859911
AllCCS	[M-H]-	142.4	32859911
AllCCS	[M+Na-2H]-	143.0	32859911
AllCCS	[M+HCOO]-	143.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.29 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0572 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.16 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1783.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	330.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	140.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	181.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	102.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	482.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	421.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	100.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1048.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	362.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1055.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	315.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	354.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	383.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	287.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	16.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dehydrozingerone	COC1=C(O)C=CC(\C=C/C(C)=O)=C1	3157.7	Standard polar	33892256
Dehydrozingerone	COC1=C(O)C=CC(\C=C/C(C)=O)=C1	1700.7	Standard non polar	33892256
Dehydrozingerone	COC1=C(O)C=CC(\C=C/C(C)=O)=C1	1838.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dehydrozingerone,1TMS,isomer #1	COC1=CC(/C=C\C(C)=O)=CC=C1O[Si](C)(C)C	1928.6	Semi standard non polar	33892256
Dehydrozingerone,1TMS,isomer #2	C=C(/C=C\C1=CC=C(O)C(OC)=C1)O[Si](C)(C)C	1985.3	Semi standard non polar	33892256
Dehydrozingerone,2TMS,isomer #1	C=C(/C=C\C1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C	2003.6	Semi standard non polar	33892256
Dehydrozingerone,2TMS,isomer #1	C=C(/C=C\C1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C	1984.8	Standard non polar	33892256
Dehydrozingerone,1TBDMS,isomer #1	COC1=CC(/C=C\C(C)=O)=CC=C1O[Si](C)(C)C(C)(C)C	2191.1	Semi standard non polar	33892256
Dehydrozingerone,1TBDMS,isomer #2	C=C(/C=C\C1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C	2251.7	Semi standard non polar	33892256
Dehydrozingerone,2TBDMS,isomer #1	C=C(/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C	2534.0	Semi standard non polar	33892256
Dehydrozingerone,2TBDMS,isomer #1	C=C(/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C	2453.0	Standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010528

KNApSAcK ID

C00053959

Chemspider ID

30654931

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

59039607

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1005791

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Agarwal M, Walia S, Dhingra S, Khambay BP: Insect growth inhibition, antifeedant and antifungal activity of compounds isolated/derived from Zingiber officinale Roscoe (ginger) rhizomes. Pest Manag Sci. 2001 Mar;57(3):289-300. [PubMed:11455660 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Dehydrozingerone (HMDB0032591)

MOL for HMDB0032591 (Dehydrozingerone)

3D MOL for HMDB0032591 (Dehydrozingerone)

3D SDF for HMDB0032591 (Dehydrozingerone)

3D-SDF for HMDB0032591 (Dehydrozingerone)

PDB for HMDB0032591 (Dehydrozingerone)

3D PDB for HMDB0032591 (Dehydrozingerone)

SMILES for HMDB0032591 (Dehydrozingerone)

INCHI for HMDB0032591 (Dehydrozingerone)

Structure for HMDB0032591 (Dehydrozingerone)

3D Structure for HMDB0032591 (Dehydrozingerone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized