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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:20 UTC

Update Date

2023-02-21 17:20:59 UTC

HMDB ID

HMDB0031610

Secondary Accession Numbers

HMDB31610

Metabolite Identification

Common Name

Allyl phenoxyacetate

Description

Allyl phenoxyacetate belongs to the class of organic compounds known as phenoxyacetic acid derivatives. Phenoxyacetic acid derivatives are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative. Allyl phenoxyacetate is a sweet, chamomile, and cocoa tasting compound. Based on a literature review a significant number of articles have been published on Allyl phenoxyacetate.

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       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.004   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.004   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.671   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.671   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.336   8.470   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      12.003   6.930   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   10                                                       
CONECT    7    5   10                                                       
CONECT    8    2   13                                                       
CONECT    9   11   14                                                       
CONECT   10    6    7   14                                                  
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13    8   11                                                       
CONECT   14    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0031610
HETATM    1  C1  UNL     1       3.586   1.243   0.754  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.253   0.130   0.472  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.565  -1.108   0.026  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.184  -0.844  -0.019  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.286  -1.809  -0.399  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.695  -2.943  -0.712  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.154  -1.517  -0.441  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.353  -0.174  -0.044  1.00  0.00           O  
HETATM    9  C6  UNL     1      -1.621   0.379   0.011  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.847   1.680   0.392  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.125   2.210   0.438  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.186   1.398   0.091  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.003   0.094  -0.296  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.697  -0.407  -0.331  1.00  0.00           C  
HETATM   15  H1  UNL     1       4.077   2.149   1.079  1.00  0.00           H  
HETATM   16  H2  UNL     1       2.509   1.256   0.659  1.00  0.00           H  
HETATM   17  H3  UNL     1       5.351   0.162   0.582  1.00  0.00           H  
HETATM   18  H4  UNL     1       3.723  -1.952   0.727  1.00  0.00           H  
HETATM   19  H5  UNL     1       3.909  -1.430  -1.000  1.00  0.00           H  
HETATM   20  H6  UNL     1      -0.691  -2.204   0.260  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.576  -1.677  -1.465  1.00  0.00           H  
HETATM   22  H8  UNL     1      -1.037   2.321   0.664  1.00  0.00           H  
HETATM   23  H9  UNL     1      -3.321   3.229   0.735  1.00  0.00           H  
HETATM   24  H10 UNL     1      -5.195   1.814   0.127  1.00  0.00           H  
HETATM   25  H11 UNL     1      -4.803  -0.566  -0.573  1.00  0.00           H  
HETATM   26  H12 UNL     1      -2.531  -1.436  -0.634  1.00  0.00           H  
CONECT    1    2    2   15   16
CONECT    2    3   17
CONECT    3    4   18   19
CONECT    4    5
CONECT    5    6    6    7
CONECT    7    8   20   21
CONECT    8    9
CONECT    9   10   10   14
CONECT   10   11   22
CONECT   11   12   12   23
CONECT   12   13   24
CONECT   13   14   14   25
CONECT   14   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Allyl phenoxyacetic acid	Generator
2-Propenyl phenoxyacetate	HMDB
Acetate p.a	HMDB
Acetate p.a.	HMDB
Acetate pa	HMDB
Acetic acid, 2-phenoxy-, 2-propen-1-yl ester	HMDB
Acetic acid, phenoxy-, 2-propenyl ester	HMDB
Acetic acid, phenoxy-, allyl ester	HMDB
FEMA 2038	HMDB
Prop-2-en-1-yl 2-phenoxyacetic acid	Generator
Allyl phenoxyacetate	MeSH

Chemical Formula

C₁₁H₁₂O₃

Average Molecular Weight

192.2112

Monoisotopic Molecular Weight

192.07864425

IUPAC Name

prop-2-en-1-yl 2-phenoxyacetate

Traditional Name

allyl phenoxyacetate

CAS Registry Number

7493-74-5

SMILES

C=CCOC(=O)COC1=CC=CC=C1

InChI Identifier

InChI=1S/C11H12O3/c1-2-8-13-11(12)9-14-10-6-4-3-5-7-10/h2-7H,1,8-9H2

InChI Key

VUFZVGQUAVDKMC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenoxyacetic acid derivatives. Phenoxyacetic acid derivatives are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenoxyacetic acid derivatives

Direct Parent

Phenoxyacetic acid derivatives

Alternative Parents

Substituents

Phenoxyacetate
Phenoxy compound
Phenol ether
Alkyl aryl ether
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031610)
Cytoplasm (HMDB: HMDB0031610)

Source

Endogenous

Endogenous (HMDB: HMDB0031610)

Exogenous

Food

Food (HMDB: HMDB0031610)

Exogenous (HMDB: HMDB0031610)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031610)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	100.00 to 102.00 °C. @ 1.00 mm Hg	The Good Scents Company Information System
Water Solubility	585 mg/L @ 20 °C (exp)	The Good Scents Company Information System
LogP	2.607 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.72 g/L	ALOGPS
logP	2.15	ALOGPS
logP	2.17	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	52.54 m³·mol⁻¹	ChemAxon
Polarizability	20.13 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]+	144.311	31661259
DarkChem	[M-H]-	141.434	31661259
DeepCCS	[M+H]+	139.711	30932474
DeepCCS	[M-H]-	136.234	30932474
DeepCCS	[M-2H]-	173.458	30932474
DeepCCS	[M+Na]+	148.996	30932474
AllCCS	[M+H]+	141.8	32859911
AllCCS	[M+H-H2O]+	137.8	32859911
AllCCS	[M+NH4]+	145.6	32859911
AllCCS	[M+Na]+	146.7	32859911
AllCCS	[M-H]-	144.2	32859911
AllCCS	[M+Na-2H]-	144.8	32859911
AllCCS	[M+HCOO]-	145.6	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.	5.8 minutes	32390414
Predicted by Siyang on May 30, 2022	14.7078 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.22 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2151.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	487.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	188.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	297.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	280.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	574.6 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	687.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	90.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1290.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	465.4 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	1305.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	393.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	398.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	457.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	437.5 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	17.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Allyl phenoxyacetate	C=CCOC(=O)COC1=CC=CC=C1	2126.5	Standard polar	33892256
Allyl phenoxyacetate	C=CCOC(=O)COC1=CC=CC=C1	1415.3	Standard non polar	33892256
Allyl phenoxyacetate	C=CCOC(=O)COC1=CC=CC=C1	1465.9	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 phenoxyacetate EI-B (Non-derivatized)	splash10-0a6u-9700000000-fd2dc283a96bf695713d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Allyl phenoxyacetate EI-B (Non-derivatized)	splash10-056u-9400000000-59e1f1260e32b874c5f0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Allyl phenoxyacetate EI-B (Non-derivatized)	splash10-0a6u-9700000000-fd2dc283a96bf695713d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Allyl phenoxyacetate EI-B (Non-derivatized)	splash10-056u-9400000000-59e1f1260e32b874c5f0	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allyl phenoxyacetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-153b91c98f5cd38e63e5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allyl phenoxyacetate 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 phenoxyacetate 10V, Positive-QTOF	splash10-0006-8900000000-b184381f391f36d38849	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl phenoxyacetate 20V, Positive-QTOF	splash10-0006-9200000000-d7d0be1d452188b36be4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl phenoxyacetate 40V, Positive-QTOF	splash10-00ke-9000000000-957617c2e08623868cad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl phenoxyacetate 10V, Negative-QTOF	splash10-000x-5900000000-4f87a1d3fd95e32d8ce2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl phenoxyacetate 20V, Negative-QTOF	splash10-0f6x-9700000000-9771cdfa0017d105b12b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl phenoxyacetate 40V, Negative-QTOF	splash10-0006-9100000000-83a27ea252cd9082f7ad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl phenoxyacetate 10V, Positive-QTOF	splash10-0007-9800000000-dc77ceee5366b674ea2e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl phenoxyacetate 20V, Positive-QTOF	splash10-000x-9200000000-49c07813a214bae48e2f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl phenoxyacetate 40V, Positive-QTOF	splash10-004i-9000000000-525dc4e8fb7042e942e7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl phenoxyacetate 10V, Negative-QTOF	splash10-0007-9000000000-7868b9fd2326cc0d03f9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl phenoxyacetate 20V, Negative-QTOF	splash10-0006-9000000000-1250e09e3aaf994c2c0f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl phenoxyacetate 40V, Negative-QTOF	splash10-0006-9000000000-cf3bbc11026980e2c1af	2021-09-25	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

FDB008246

KNApSAcK ID

Not Available

Chemspider ID

22542

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24117

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1028371

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 phenoxyacetate (HMDB0031610)

MOL for HMDB0031610 (Allyl phenoxyacetate)

3D MOL for HMDB0031610 (Allyl phenoxyacetate)

3D SDF for HMDB0031610 (Allyl phenoxyacetate)

3D-SDF for HMDB0031610 (Allyl phenoxyacetate)

PDB for HMDB0031610 (Allyl phenoxyacetate)

3D PDB for HMDB0031610 (Allyl phenoxyacetate)

SMILES for HMDB0031610 (Allyl phenoxyacetate)

INCHI for HMDB0031610 (Allyl phenoxyacetate)

Structure for HMDB0031610 (Allyl phenoxyacetate)

3D Structure for HMDB0031610 (Allyl phenoxyacetate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra