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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:09:09 UTC

Update Date

2023-02-21 17:28:24 UTC

HMDB ID

HMDB0040592

Secondary Accession Numbers

HMDB40592

Metabolite Identification

Common Name

Allyl benzoate

Description

Allyl benzoate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Allyl benzoate is a sweet, berry, and cherry tasting compound. Based on a literature review very few articles have been published on Allyl benzoate.

Structure

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

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       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    8                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    9                                                       
CONECT    7    5    9                                                       
CONECT    8    2   12                                                       
CONECT    9    6    7   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12    8   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Allyl benzoic acid	Generator
2-Propenyl benzoate	HMDB
3-Dimethylallyl-4-hydroxybenzoate	HMDB
Benzoic acid, 2-propenyl ester	HMDB
Benzoic acid, allyl ester	HMDB
Benzoic acid, allyl ester (8ci)	HMDB
Benzoylacrylic acid	HMDB
Prop-2-en-1-yl benzoic acid	Generator

Chemical Formula

C₁₀H₁₀O₂

Average Molecular Weight

162.1852

Monoisotopic Molecular Weight

162.068079564

IUPAC Name

prop-2-en-1-yl benzoate

Traditional Name

prop-2-en-1-yl benzoate

CAS Registry Number

583-04-0

SMILES

C=CCOC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C10H10O2/c1-2-8-12-10(11)9-6-4-3-5-7-9/h2-7H,1,8H2

InChI Key

LYJHVEDILOKZCG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoyl
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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: HMDB0040592)
Cytoplasm (HMDB: HMDB0040592)

Source

Exogenous

Exogenous (HMDB: HMDB0040592)

Food

Food (HMDB: HMDB0040592)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040592)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	82.00 to 85.00 °C. @ 5.00 mm Hg	The Good Scents Company Information System
Water Solubility	348.1 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.024 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.46 g/L	ALOGPS
logP	2.5	ALOGPS
logP	2.71	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	47.25 m³·mol⁻¹	ChemAxon
Polarizability	17.37 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	136.908	31661259
DarkChem	[M-H]-	132.498	31661259
DeepCCS	[M+H]+	134.754	30932474
DeepCCS	[M-H]-	130.95	30932474
DeepCCS	[M-2H]-	168.544	30932474
DeepCCS	[M+Na]+	144.083	30932474
AllCCS	[M+H]+	134.1	32859911
AllCCS	[M+H-H2O]+	129.7	32859911
AllCCS	[M+NH4]+	138.2	32859911
AllCCS	[M+Na]+	139.4	32859911
AllCCS	[M-H]-	134.3	32859911
AllCCS	[M+Na-2H]-	135.3	32859911
AllCCS	[M+HCOO]-	136.4	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.	6.94 minutes	32390414
Predicted by Siyang on May 30, 2022	15.5978 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.31 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2376.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	540.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	210.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	367.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	388.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	639.8 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	736.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	150.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1333.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	469.7 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	1439.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	427.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	524.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	513.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	458.7 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	53.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Allyl benzoate	C=CCOC(=O)C1=CC=CC=C1	1956.3	Standard polar	33892256
Allyl benzoate	C=CCOC(=O)C1=CC=CC=C1	1224.0	Standard non polar	33892256
Allyl benzoate	C=CCOC(=O)C1=CC=CC=C1	1294.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Allyl benzoate EI-B (Non-derivatized)	splash10-0a4i-6900000000-ff25aa923c8a2f7b4cc1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Allyl benzoate EI-B (Non-derivatized)	splash10-0a4i-6900000000-ff25aa923c8a2f7b4cc1	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allyl benzoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-5900000000-78bc52646a968124e32f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allyl benzoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl benzoate 10V, Positive-QTOF	splash10-03dl-3900000000-d6a618b80c073b728f8b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl benzoate 20V, Positive-QTOF	splash10-0006-9300000000-5f8469a47af307b9f139	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl benzoate 40V, Positive-QTOF	splash10-052f-9200000000-d399851e98ce6ad25ceb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl benzoate 10V, Negative-QTOF	splash10-03di-2900000000-f200d70ab4abccbe5fd1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl benzoate 20V, Negative-QTOF	splash10-00fr-5900000000-38ab39d9533dfb81d6ed	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl benzoate 40V, Negative-QTOF	splash10-004i-9200000000-5eac4d782d336a2e08bf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl benzoate 10V, Negative-QTOF	splash10-03di-2900000000-af1feee5a40f6c587b3d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl benzoate 20V, Negative-QTOF	splash10-004i-9300000000-2b146144403b298ba656	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl benzoate 40V, Negative-QTOF	splash10-004i-9000000000-ef0b8d9bda19c5a5c003	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl benzoate 10V, Positive-QTOF	splash10-0ab9-2900000000-3fb2fca4f493202f548b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl benzoate 20V, Positive-QTOF	splash10-0a4i-4900000000-74c5dbfa8892bac6bee6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl benzoate 40V, Positive-QTOF	splash10-056r-9500000000-85b23c4b65ae67253af5	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

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

FDB020375

KNApSAcK ID

Not Available

Chemspider ID

21391694

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11406

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1009751

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Allyl benzoate (HMDB0040592)

MOL for HMDB0040592 (Allyl benzoate)

3D MOL for HMDB0040592 (Allyl benzoate)

3D SDF for HMDB0040592 (Allyl benzoate)

3D-SDF for HMDB0040592 (Allyl benzoate)

PDB for HMDB0040592 (Allyl benzoate)

3D PDB for HMDB0040592 (Allyl benzoate)

SMILES for HMDB0040592 (Allyl benzoate)

INCHI for HMDB0040592 (Allyl benzoate)

Structure for HMDB0040592 (Allyl benzoate)

3D Structure for HMDB0040592 (Allyl benzoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra