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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:18:27 UTC

Update Date

2023-02-21 17:28:27 UTC

HMDB ID

HMDB0040730

Secondary Accession Numbers

HMDB40730

Metabolite Identification

Common Name

Butyl salicylate

Description

Butyl salicylate belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group. Butyl salicylate is a clover, ethyl benzoate, and harsh tasting compound. Butyl salicylate has been detected, but not quantified in, fruits. This could make butyl salicylate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Butyl salicylate.

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   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.337   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.337  10.780   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003  11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.336  11.550   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       9.336   6.930   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       8.002   9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    8                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    9                                                       
CONECT    7    5   10                                                       
CONECT    8    3   14                                                       
CONECT    9    6   10   11                                                  
CONECT   10    7    9   12                                                  
CONECT   11    9   13   14                                                  
CONECT   12   10                                                            
CONECT   13   11                                                            
CONECT   14    8   11                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0040730
HETATM    1  C1  UNL     1       3.595  -1.031  -0.531  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.775   0.191  -0.889  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.559   0.968   0.392  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.834   0.170   1.429  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.553  -0.267   1.039  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.462   0.636   0.699  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.131   1.838   0.773  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.768   0.129   0.302  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.963  -1.262   0.276  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.176  -1.787  -0.091  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.241  -0.990  -0.445  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.064   0.365  -0.423  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.825   0.927  -0.049  1.00  0.00           C  
HETATM   14  O3  UNL     1      -2.704   2.298  -0.045  1.00  0.00           O  
HETATM   15  H1  UNL     1       4.308  -0.724   0.270  1.00  0.00           H  
HETATM   16  H2  UNL     1       4.191  -1.379  -1.379  1.00  0.00           H  
HETATM   17  H3  UNL     1       2.919  -1.785  -0.097  1.00  0.00           H  
HETATM   18  H4  UNL     1       3.319   0.826  -1.616  1.00  0.00           H  
HETATM   19  H5  UNL     1       1.803  -0.125  -1.288  1.00  0.00           H  
HETATM   20  H6  UNL     1       3.592   1.147   0.812  1.00  0.00           H  
HETATM   21  H7  UNL     1       2.119   1.949   0.230  1.00  0.00           H  
HETATM   22  H8  UNL     1       1.716   0.835   2.336  1.00  0.00           H  
HETATM   23  H9  UNL     1       2.484  -0.655   1.736  1.00  0.00           H  
HETATM   24  H10 UNL     1      -1.115  -1.884   0.557  1.00  0.00           H  
HETATM   25  H11 UNL     1      -3.295  -2.856  -0.102  1.00  0.00           H  
HETATM   26  H12 UNL     1      -5.200  -1.451  -0.734  1.00  0.00           H  
HETATM   27  H13 UNL     1      -4.866   1.030  -0.691  1.00  0.00           H  
HETATM   28  H14 UNL     1      -1.959   2.887   0.174  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3   18   19
CONECT    3    4   20   21
CONECT    4    5   22   23
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9    9   13
CONECT    9   10   24
CONECT   10   11   11   25
CONECT   11   12   26
CONECT   12   13   13   27
CONECT   13   14
CONECT   14   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Butyl salicylic acid	Generator
2-Hydroxy-benzoic acid, butyl ester	HMDB
Benzoic acid, 2-hydroxy-, butyl ester	HMDB
Benzoic acid, hydroxy-, butyl ester	HMDB
Brunol	HMDB
Butyl (2-hydroxyphenyl)formate	HMDB
Butyl 2-hydroxybenzoate	HMDB
Butyl hydroxybenzoate	HMDB
Butyl O-hydroxybenzoate	HMDB
FEMA 3650	HMDB
N-Butyl O-hydroxybenzoate	HMDB
N-Butyl salicylate	HMDB
Salicylic acid N-butyl ester	HMDB
Salicylic acid, butyl ester	HMDB
Butyl 2-hydroxybenzoic acid	Generator
Butyl salicylate	MeSH

Chemical Formula

C₁₁H₁₄O₃

Average Molecular Weight

194.2271

Monoisotopic Molecular Weight

194.094294314

IUPAC Name

butyl 2-hydroxybenzoate

Traditional Name

butyl 2-hydroxybenzoate

CAS Registry Number

2052-14-4

SMILES

CCCCOC(=O)C1=CC=CC=C1O

InChI Identifier

InChI=1S/C11H14O3/c1-2-3-8-14-11(13)9-6-4-5-7-10(9)12/h4-7,12H,2-3,8H2,1H3

InChI Key

YFDUWSBGVPBWKF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

o-Hydroxybenzoic acid esters

Alternative Parents

Substituents

O-hydroxybenzoic acid ester
Salicylic acid or derivatives
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
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

Cellular substructure

Membrane (HMDB: HMDB0040730)
Cell membrane (HMDB: HMDB0040730)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040730)

Source

Exogenous

Exogenous (HMDB: HMDB0040730)

Food

Food (HMDB: HMDB0040730)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0040730)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040730)

Biological role

Nutrient (HMDB: HMDB0040730)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	6 °C	Not Available
Boiling Point	271.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	19.8 mg/L @ 25 °C (exp)	The Good Scents Company Information System
LogP	4.63	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.54 g/L	ALOGPS
logP	3.6	ALOGPS
logP	3.65	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9.72	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	53.94 m³·mol⁻¹	ChemAxon
Polarizability	21.28 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
DarkChem	[M+H]+	144.4	31661259
DarkChem	[M-H]-	140.355	31661259
DeepCCS	[M+H]+	147.252	30932474
DeepCCS	[M-H]-	143.93	30932474
DeepCCS	[M-2H]-	180.9	30932474
DeepCCS	[M+Na]+	156.343	30932474
AllCCS	[M+H]+	144.0	32859911
AllCCS	[M+H-H2O]+	140.0	32859911
AllCCS	[M+NH4]+	147.7	32859911
AllCCS	[M+Na]+	148.8	32859911
AllCCS	[M-H]-	145.8	32859911
AllCCS	[M+Na-2H]-	146.6	32859911
AllCCS	[M+HCOO]-	147.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Butyl salicylate	CCCCOC(=O)C1=CC=CC=C1O	2178.2	Standard polar	33892256
Butyl salicylate	CCCCOC(=O)C1=CC=CC=C1O	1516.6	Standard non polar	33892256
Butyl salicylate	CCCCOC(=O)C1=CC=CC=C1O	1511.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Butyl salicylate,1TMS,isomer #1	CCCCOC(=O)C1=CC=CC=C1O[Si](C)(C)C	1649.7	Semi standard non polar	33892256
Butyl salicylate,1TBDMS,isomer #1	CCCCOC(=O)C1=CC=CC=C1O[Si](C)(C)C(C)(C)C	1871.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Butyl salicylate EI-B (Non-derivatized)	splash10-00di-5900000000-6067ba05f2403e53bd30	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butyl salicylate EI-B (Non-derivatized)	splash10-00di-3900000000-efe18a9589df0537f04f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butyl salicylate EI-B (Non-derivatized)	splash10-00di-5900000000-8c363d7b843ec30dd80a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butyl salicylate EI-B (Non-derivatized)	splash10-00di-4900000000-ecc73d6f1204d08019f2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butyl salicylate EI-B (Non-derivatized)	splash10-00di-5900000000-6067ba05f2403e53bd30	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butyl salicylate EI-B (Non-derivatized)	splash10-00di-3900000000-efe18a9589df0537f04f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butyl salicylate EI-B (Non-derivatized)	splash10-00di-5900000000-8c363d7b843ec30dd80a	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butyl salicylate EI-B (Non-derivatized)	splash10-00di-4900000000-ecc73d6f1204d08019f2	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butyl salicylate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-4900000000-713f351b660137cec24a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butyl salicylate GC-MS (1 TMS) - 70eV, Positive	splash10-0006-4910000000-eedddc8abf5bc65b2136	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butyl salicylate 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 - Butyl salicylate 10V, Positive-QTOF	splash10-0002-3900000000-89dec723070b6953f5bf	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl salicylate 20V, Positive-QTOF	splash10-0ab9-9500000000-06c239abd3c9d21c1cf8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl salicylate 40V, Positive-QTOF	splash10-0zml-9200000000-65fd7d950aa3eb4d1735	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl salicylate 10V, Negative-QTOF	splash10-0006-2900000000-e55112850130e746463f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl salicylate 20V, Negative-QTOF	splash10-000f-7900000000-23cf4f0f58655781afc1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl salicylate 40V, Negative-QTOF	splash10-0006-9100000000-8ec988134670bd348c76	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl salicylate 10V, Positive-QTOF	splash10-00b9-0900000000-f424237b02a6eaaed279	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl salicylate 20V, Positive-QTOF	splash10-00di-3900000000-702198017f16931141ed	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl salicylate 40V, Positive-QTOF	splash10-0gbc-9100000000-88309e8532eb7453570e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl salicylate 10V, Negative-QTOF	splash10-0006-9800000000-3a7ddae028240a6979e5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl salicylate 20V, Negative-QTOF	splash10-0006-9200000000-153233321cd202ebac38	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl salicylate 40V, Negative-QTOF	splash10-0006-9000000000-1af6aa42c36a40364126	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+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

FDB020539

KNApSAcK ID

C00054077

Chemspider ID

15495

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16330

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1013802

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 Butyl salicylate (HMDB0040730)

MOL for HMDB0040730 (Butyl salicylate)

3D MOL for HMDB0040730 (Butyl salicylate)

3D SDF for HMDB0040730 (Butyl salicylate)

3D-SDF for HMDB0040730 (Butyl salicylate)

PDB for HMDB0040730 (Butyl salicylate)

3D PDB for HMDB0040730 (Butyl salicylate)

SMILES for HMDB0040730 (Butyl salicylate)

INCHI for HMDB0040730 (Butyl salicylate)

Structure for HMDB0040730 (Butyl salicylate)

3D Structure for HMDB0040730 (Butyl salicylate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra