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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:42:15 UTC

Update Date

2023-02-21 17:20:20 UTC

HMDB ID

HMDB0031311

Secondary Accession Numbers

HMDB31311

Metabolite Identification

Common Name

Benzyl butyl ether

Description

Benzyl butyl ether belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene). Benzyl butyl ether is a floral and rose tasting compound. Benzyl butyl ether has been detected, but not quantified in, several different foods, such as common mushrooms (Agaricus bisporus), mushrooms, nuts, and oyster mushrooms (Pleurotus ostreatus). This could make benzyl butyl ether a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Benzyl butyl ether.

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       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.004   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.004   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.671   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.671   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.669   6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    9                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   11                                                       
CONECT    8    6   11                                                       
CONECT    9    3   12                                                       
CONECT   10   11   12                                                       
CONECT   11    7    8   10                                                  
CONECT   12    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

COMPND    HMDB0031311
HETATM    1  C1  UNL     1      -4.986   0.516   0.152  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.781  -0.240  -0.368  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.507   0.412   0.164  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.337  -0.377  -0.383  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.118   0.110   0.023  1.00  0.00           O  
HETATM    6  C5  UNL     1       0.890  -0.651  -0.508  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.242  -0.208  -0.130  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.516   0.864   0.677  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.830   1.187   0.965  1.00  0.00           C  
HETATM   10  C9  UNL     1       4.890   0.460   0.461  1.00  0.00           C  
HETATM   11  C10 UNL     1       4.626  -0.612  -0.347  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.312  -0.929  -0.629  1.00  0.00           C  
HETATM   13  H1  UNL     1      -5.399   0.024   1.040  1.00  0.00           H  
HETATM   14  H2  UNL     1      -5.789   0.501  -0.626  1.00  0.00           H  
HETATM   15  H3  UNL     1      -4.713   1.581   0.308  1.00  0.00           H  
HETATM   16  H4  UNL     1      -3.873  -1.276   0.009  1.00  0.00           H  
HETATM   17  H5  UNL     1      -3.832  -0.248  -1.458  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.566   0.324   1.268  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.470   1.482  -0.080  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.366  -0.421  -1.487  1.00  0.00           H  
HETATM   21  H9  UNL     1      -1.457  -1.420   0.025  1.00  0.00           H  
HETATM   22  H10 UNL     1       0.802  -0.578  -1.629  1.00  0.00           H  
HETATM   23  H11 UNL     1       0.795  -1.730  -0.277  1.00  0.00           H  
HETATM   24  H12 UNL     1       1.684   1.432   1.070  1.00  0.00           H  
HETATM   25  H13 UNL     1       4.054   2.046   1.612  1.00  0.00           H  
HETATM   26  H14 UNL     1       5.930   0.715   0.687  1.00  0.00           H  
HETATM   27  H15 UNL     1       5.466  -1.167  -0.730  1.00  0.00           H  
HETATM   28  H16 UNL     1       3.159  -1.797  -1.281  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16   17
CONECT    3    4   18   19
CONECT    4    5   20   21
CONECT    5    6
CONECT    6    7   22   23
CONECT    7    8    8   12
CONECT    8    9   24
CONECT    9   10   10   25
CONECT   10   11   26
CONECT   11   12   12   27
CONECT   12   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Butoxymethyl)-benzene	HMDB
(Butoxymethyl)benzene	HMDB
(Butoxymethyl)benzene, 9ci	HMDB
1-Benzyloxybutane	HMDB
a-Butoxytoluene	HMDB
Benzyl N-butyl ether	HMDB
Butoxy toluene	HMDB
Butyl benzyl ether	HMDB
Ether, benzyl butyl	HMDB
Ether, benzyl N-butyl	HMDB
FEMA 2139	HMDB
N-Butyl benzyl ether	HMDB

Chemical Formula

C₁₁H₁₆O

Average Molecular Weight

164.2441

Monoisotopic Molecular Weight

164.120115134

IUPAC Name

(butoxymethyl)benzene

Traditional Name

benzene, (butoxymethyl)-

CAS Registry Number

588-67-0

SMILES

CCCCOCC1=CC=CC=C1

InChI Identifier

InChI=1S/C11H16O/c1-2-3-9-12-10-11-7-5-4-6-8-11/h4-8H,2-3,9-10H2,1H3

InChI Key

MAYUYFCAPVDYBQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzylethers

Direct Parent

Benzylethers

Alternative Parents

Substituents

Benzylether
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Membrane (HMDB: HMDB0031311)
Cell membrane (HMDB: HMDB0031311)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031311)

Source

Endogenous

Endogenous (HMDB: HMDB0031311)

Plant

Plant (HMDB: HMDB0031311)

Exogenous

Food

Food (HMDB: HMDB0031311)

Vegetable

Mushroom

Nut

Nuts (FooDB: FOOD00869)

Exogenous (HMDB: HMDB0031311)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031311)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	220.00 to 224.00 °C. @ 744.00 mm Hg	The Good Scents Company Information System
Water Solubility	110.1 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.372 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.032 g/L	ALOGPS
logP	3.32	ALOGPS
logP	3.17	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	51.5 m³·mol⁻¹	ChemAxon
Polarizability	20.26 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]+	136.65	31661259
DarkChem	[M-H]-	132.729	31661259
DeepCCS	[M+H]+	141.195	30932474
DeepCCS	[M-H]-	137.437	30932474
DeepCCS	[M-2H]-	175.186	30932474
DeepCCS	[M+Na]+	150.512	30932474
AllCCS	[M+H]+	137.0	32859911
AllCCS	[M+H-H2O]+	132.7	32859911
AllCCS	[M+NH4]+	140.9	32859911
AllCCS	[M+Na]+	142.1	32859911
AllCCS	[M-H]-	141.7	32859911
AllCCS	[M+Na-2H]-	143.0	32859911
AllCCS	[M+HCOO]-	144.5	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.	7.29 minutes	32390414
Predicted by Siyang on May 30, 2022	17.5766 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.9 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2441.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	621.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	237.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	398.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	370.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	761.7 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	781.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	133.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1554.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	537.1 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	1513.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	526.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	463.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	506.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	514.7 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	13.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzyl butyl ether	CCCCOCC1=CC=CC=C1	1619.5	Standard polar	33892256
Benzyl butyl ether	CCCCOCC1=CC=CC=C1	1258.7	Standard non polar	33892256
Benzyl butyl ether	CCCCOCC1=CC=CC=C1	1247.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Benzyl butyl ether EI-B (Non-derivatized)	splash10-0006-9000000000-4c4bbf1c0ee9e3e9d307	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzyl butyl ether EI-B (Non-derivatized)	splash10-0006-9000000000-4c4bbf1c0ee9e3e9d307	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzyl butyl ether GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-488c1c416360f6571b8d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzyl butyl ether 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 - Benzyl butyl ether 10V, Positive-QTOF	splash10-014i-6900000000-6b48e61198e490705e89	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl butyl ether 20V, Positive-QTOF	splash10-0a4l-9200000000-f2f33ffc6fcd60d5b243	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl butyl ether 40V, Positive-QTOF	splash10-0006-9000000000-55294dc7ce867773ee03	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl butyl ether 10V, Negative-QTOF	splash10-03di-2900000000-2285fdf7dd76b28f0569	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl butyl ether 20V, Negative-QTOF	splash10-08fr-6900000000-479fb2a9f22ea01a234d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl butyl ether 40V, Negative-QTOF	splash10-056r-9200000000-51189d4f11a411c1af0d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl butyl ether 10V, Negative-QTOF	splash10-03di-0900000000-ca1b8ca24a2e14bac2d6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl butyl ether 20V, Negative-QTOF	splash10-0006-9300000000-ac214538dcb05d6370b6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl butyl ether 40V, Negative-QTOF	splash10-004i-9000000000-f12b3549172a59940a67	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl butyl ether 10V, Positive-QTOF	splash10-0006-9000000000-83a09b110c49b2194d37	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl butyl ether 20V, Positive-QTOF	splash10-0006-9000000000-6dd96e9fb7d3c24100cd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl butyl ether 40V, Positive-QTOF	splash10-0006-9000000000-2bedc96d048f8f6ce846	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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

FDB003368

KNApSAcK ID

Not Available

Chemspider ID

55081

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61134

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1033051

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Wu HH, Tian L, Chen G, Xu N, Wang YN, Sun S, Pei YH: Six compounds from marine fungus Y26-02. J Asian Nat Prod Res. 2009 Aug;11(8):748-51. doi: 10.1080/10286020903025783. [PubMed:20183318 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Benzyl butyl ether (HMDB0031311)

MOL for HMDB0031311 (Benzyl butyl ether)

3D MOL for HMDB0031311 (Benzyl butyl ether)

3D SDF for HMDB0031311 (Benzyl butyl ether)

3D-SDF for HMDB0031311 (Benzyl butyl ether)

PDB for HMDB0031311 (Benzyl butyl ether)

3D PDB for HMDB0031311 (Benzyl butyl ether)

SMILES for HMDB0031311 (Benzyl butyl ether)

INCHI for HMDB0031311 (Benzyl butyl ether)

Structure for HMDB0031311 (Benzyl butyl ether)

3D Structure for HMDB0031311 (Benzyl butyl ether)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra