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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:31:11 UTC

Update Date

2023-02-21 17:25:45 UTC

HMDB ID

HMDB0037277

Secondary Accession Numbers

HMDB37277

Metabolite Identification

Common Name

Isoeugenol formate

Description

Isoeugenol formate belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Isoeugenol formate is a sweet, clove, and green tasting compound. Based on a literature review very few articles have been published on Isoeugenol formate.

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      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -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       2.667   4.620   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       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   13                                                            
CONECT    3    1    4                                                       
CONECT    4    3    9                                                       
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    9   11                                                       
CONECT    8   12   14                                                       
CONECT    9    4    5    7                                                  
CONECT   10    6   11   14                                                  
CONECT   11    7   10   13                                                  
CONECT   12    8                                                            
CONECT   13    2   11                                                       
CONECT   14    8   10                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0037277
HETATM    1  C1  UNL     1       3.673   0.943   0.114  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.374  -0.480  -0.047  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.179  -0.969   0.087  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.979  -0.258   0.409  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.822   0.995   0.879  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.468   1.531   1.052  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.611   0.828   0.762  1.00  0.00           C  
HETATM    8  O1  UNL     1      -2.862   1.391   0.946  1.00  0.00           O  
HETATM    9  C8  UNL     1      -3.506   2.106  -0.056  1.00  0.00           C  
HETATM   10  O2  UNL     1      -2.876   2.213  -1.158  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.465  -0.451   0.284  1.00  0.00           C  
HETATM   12  O3  UNL     1      -2.589  -1.203  -0.024  1.00  0.00           O  
HETATM   13  C10 UNL     1      -2.477  -2.507  -0.512  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.208  -0.977   0.113  1.00  0.00           C  
HETATM   15  H1  UNL     1       4.724   1.076  -0.372  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.067   1.633  -0.499  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.844   1.272   1.154  1.00  0.00           H  
HETATM   18  H4  UNL     1       4.225  -1.193  -0.299  1.00  0.00           H  
HETATM   19  H5  UNL     1       2.116  -2.092  -0.059  1.00  0.00           H  
HETATM   20  H6  UNL     1       1.653   1.603   1.167  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.570   2.535   1.428  1.00  0.00           H  
HETATM   22  H8  UNL     1      -4.486   2.546   0.090  1.00  0.00           H  
HETATM   23  H9  UNL     1      -2.143  -3.211   0.278  1.00  0.00           H  
HETATM   24  H10 UNL     1      -1.778  -2.512  -1.385  1.00  0.00           H  
HETATM   25  H11 UNL     1      -3.469  -2.833  -0.900  1.00  0.00           H  
HETATM   26  H12 UNL     1      -0.149  -1.985  -0.267  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    3   18
CONECT    3    4   19
CONECT    4    5    5   14
CONECT    5    6   20
CONECT    6    7    7   21
CONECT    7    8   11
CONECT    8    9
CONECT    9   10   10   22
CONECT   11   12   14   14
CONECT   12   13
CONECT   13   23   24   25
CONECT   14   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Isoeugenol formic acid	Generator
2-Methoxy-4-(1-propen-1-yl)phenyl formate	HMDB
2-Methoxy-4-(1-propenyl)phenyl formate	HMDB
2-Methoxy-4-propenylphenyl formate	HMDB
4-(1-Propen-1-yl)-2-methoxyphenyl formate	HMDB
FEMA 2474	HMDB
Isoeugenyl formate	HMDB
Phenol, 2-methoxy-4-(1-propenyl)-, formate	HMDB
Phenol, 2-methoxy-4-propenyl, formate	HMDB
2-Methoxy-4-[(1Z)-prop-1-en-1-yl]phenyl formic acid	Generator

Chemical Formula

C₁₁H₁₂O₃

Average Molecular Weight

192.2112

Monoisotopic Molecular Weight

192.07864425

IUPAC Name

2-methoxy-4-[(1Z)-prop-1-en-1-yl]phenyl formate

Traditional Name

2-methoxy-4-[(1Z)-prop-1-en-1-yl]phenyl formate

CAS Registry Number

7774-96-1

SMILES

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

InChI Identifier

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

InChI Key

QUUXIMKMPYPPDM-ARJAWSKDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Anisole
Methoxybenzene
Styrene
Alkyl aryl ether
Monocyclic benzene moiety
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0037277)
Cell membrane (HMDB: HMDB0037277)

Source

Exogenous

Exogenous (HMDB: HMDB0037277)

Food

Food (HMDB: HMDB0037277)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037277)

Biological role

Nutrient (HMDB: HMDB0037277)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	282.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	2.330 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.082 g/L	ALOGPS
logP	3.16	ALOGPS
logP	2.5	ChemAxon
logS	-3.4	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	4	ChemAxon
Refractivity	54.52 m³·mol⁻¹	ChemAxon
Polarizability	20.03 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]+	144.601	31661259
DarkChem	[M-H]-	140.801	31661259
DeepCCS	[M+H]+	141.764	30932474
DeepCCS	[M-H]-	139.176	30932474
DeepCCS	[M-2H]-	174.689	30932474
DeepCCS	[M+Na]+	149.943	30932474
AllCCS	[M+H]+	141.9	32859911
AllCCS	[M+H-H2O]+	137.6	32859911
AllCCS	[M+NH4]+	145.8	32859911
AllCCS	[M+Na]+	146.9	32859911
AllCCS	[M-H]-	142.8	32859911
AllCCS	[M+Na-2H]-	143.4	32859911
AllCCS	[M+HCOO]-	144.1	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.	6.17 minutes	32390414
Predicted by Siyang on May 30, 2022	12.3627 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.96 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1836.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	375.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	154.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	221.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	105.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	459.4 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	463.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	106.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1082.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	410.8 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	1025.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	317.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	381.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	366.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	310.8 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	9.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoeugenol formate	COC1=C(OC=O)C=CC(\C=C/C)=C1	2495.8	Standard polar	33892256
Isoeugenol formate	COC1=C(OC=O)C=CC(\C=C/C)=C1	1559.0	Standard non polar	33892256
Isoeugenol formate	COC1=C(OC=O)C=CC(\C=C/C)=C1	1646.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isoeugenol formate GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-0900000000-6b15f8fa2dd9126993c4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoeugenol formate 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 - Isoeugenol formate 10V, Positive-QTOF	splash10-0006-0900000000-d2f573c99e30f54c1483	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenol formate 20V, Positive-QTOF	splash10-0007-2900000000-f9b5b475e48dd47d22aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenol formate 40V, Positive-QTOF	splash10-00l7-9800000000-201bea885a4e3b6d0592	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenol formate 10V, Negative-QTOF	splash10-0006-0900000000-5faa45acd6ecc52fc2b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenol formate 20V, Negative-QTOF	splash10-0006-2900000000-b83e6da40a341f1d8bf6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenol formate 40V, Negative-QTOF	splash10-0006-9500000000-74dcc7c758163fee74d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenol formate 10V, Positive-QTOF	splash10-00m0-0900000000-8c607c1541e02dba67bb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenol formate 20V, Positive-QTOF	splash10-001i-0900000000-6ffbd4cc538d0dbb8afe	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenol formate 40V, Positive-QTOF	splash10-016r-8900000000-40ebda1d4df639fee53f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenol formate 10V, Negative-QTOF	splash10-03dm-0900000000-e311db4bf15032428d42	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenol formate 20V, Negative-QTOF	splash10-000t-0900000000-d6b1a0f1a1627dcbae09	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenol formate 40V, Negative-QTOF	splash10-00kv-6900000000-a6357e854afd98fdda9b	2021-09-24	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

Membrane

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

FDB016295

KNApSAcK ID

Not Available

Chemspider ID

20127079

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20831812

PDB ID

Not Available

ChEBI ID

173925

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1023541

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 Isoeugenol formate (HMDB0037277)

MOL for HMDB0037277 (Isoeugenol formate)

3D MOL for HMDB0037277 (Isoeugenol formate)

3D SDF for HMDB0037277 (Isoeugenol formate)

3D-SDF for HMDB0037277 (Isoeugenol formate)

PDB for HMDB0037277 (Isoeugenol formate)

3D PDB for HMDB0037277 (Isoeugenol formate)

SMILES for HMDB0037277 (Isoeugenol formate)

INCHI for HMDB0037277 (Isoeugenol formate)

Structure for HMDB0037277 (Isoeugenol formate)

3D Structure for HMDB0037277 (Isoeugenol formate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra