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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:59:17 UTC

Update Date

2023-02-21 17:28:17 UTC

HMDB ID

HMDB0040446

Secondary Accession Numbers

HMDB40446

Metabolite Identification

Common Name

Benzyl acetoacetate

Description

Benzyl acetoacetate belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group. Benzyl acetoacetate is a sweet, benzyl acetate, and benzyl propionate tasting compound. Based on a literature review very few articles have been published on Benzyl acetoacetate.

Structure

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


  Mrv0541 05061311502D          

 14 14  0  0  0  0            999 V2000
   -6.6730   -0.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9585    0.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9585    0.9945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2440   -0.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5296    0.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5296    0.9945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8151   -0.2430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1006    0.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3862   -0.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6717    0.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9572   -0.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9572   -1.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6717   -1.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3862   -1.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  2  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040446

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)CC(=O)OCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O3/c1-9(12)7-11(13)14-8-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3

> <INCHI_KEY>
WOFAGNLBCJWEOE-UHFFFAOYSA-N

> <FORMULA>
C11H12O3

> <MOLECULAR_WEIGHT>
192.2112

> <EXACT_MASS>
192.07864425

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
19.847123634927442

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
benzyl 3-oxobutanoate

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
1.8688754276666666

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.34406525126412

> <JCHEM_PKA_STRONGEST_BASIC>
-6.968304811509863

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
51.92060000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzyl 3-oxobutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

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     -12.456  -0.454   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.123   0.316   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0     -11.123   1.856   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -9.789  -0.454   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.455   0.316   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -8.455   1.856   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -7.122  -0.454   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.788   0.316   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.454  -0.454   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.121   0.317   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.787  -0.453   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.787  -1.993   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.121  -2.763   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.454  -1.994   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14    9   13                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Benzyl acetoacetic acid	Generator
Ac-benzyl	HMDB
Acetoacetic acid benzyl ester	HMDB
Acetoacetic acid, benzyl ester	HMDB
Acetoacetic acid, benzyl ester (8ci)	HMDB
Benzyl 3-oxobutanoate	HMDB
Benzyl acetylacetate	HMDB
Benzyl beta-ketobutyrate	HMDB
Butanoic acid, 3-oxo-, phenylmethyl ester	HMDB
FEMA 2136	HMDB
Phenylmethyl 3-oxobutanoate	HMDB
Benzyl 3-oxobutanoic acid	Generator

Chemical Formula

C₁₁H₁₂O₃

Average Molecular Weight

192.2112

Monoisotopic Molecular Weight

192.07864425

IUPAC Name

benzyl 3-oxobutanoate

Traditional Name

benzyl 3-oxobutanoate

CAS Registry Number

5396-89-4

SMILES

CC(=O)CC(=O)OCC1=CC=CC=C1

InChI Identifier

InChI=1S/C11H12O3/c1-9(12)7-11(13)14-8-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3

InChI Key

WOFAGNLBCJWEOE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzyloxycarbonyls

Direct Parent

Benzyloxycarbonyls

Alternative Parents

Substituents

Benzyloxycarbonyl
Beta-keto acid
Fatty acid ester
Fatty acyl
1,3-dicarbonyl compound
Keto acid
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Exogenous (HMDB: HMDB0040446)

Food

Food (HMDB: HMDB0040446)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040446)

Biological role

Nutrient (HMDB: HMDB0040446)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	162.00 to 164.00 °C. @ 16.00 mm Hg	The Good Scents Company Information System
Boiling Point	156.00 to 159.00 °C. @ 10.00 mm Hg	The Good Scents Company Information System
Water Solubility	6531 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.599 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.45 g/L	ALOGPS
logP	1.42	ALOGPS
logP	1.87	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	10.34	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	51.92 m³·mol⁻¹	ChemAxon
Polarizability	19.85 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]+	146.906	31661259
DarkChem	[M-H]-	143.364	31661259
DeepCCS	[M+H]+	137.344	30932474
DeepCCS	[M-H]-	134.786	30932474
DeepCCS	[M-2H]-	170.424	30932474
DeepCCS	[M+Na]+	145.73	30932474
AllCCS	[M+H]+	141.8	32859911
AllCCS	[M+H-H2O]+	137.8	32859911
AllCCS	[M+NH4]+	145.5	32859911
AllCCS	[M+Na]+	146.6	32859911
AllCCS	[M-H]-	144.2	32859911
AllCCS	[M+Na-2H]-	144.9	32859911
AllCCS	[M+HCOO]-	145.8	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.	6.98 minutes	32390414
Predicted by Siyang on May 30, 2022	13.2542 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.42 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1984.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	422.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	163.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	241.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	122.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	508.9 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	552.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	71.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1149.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	412.4 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	1252.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	345.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	372.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	371.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	312.4 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	35.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzyl acetoacetate	CC(=O)CC(=O)OCC1=CC=CC=C1	2396.5	Standard polar	33892256
Benzyl acetoacetate	CC(=O)CC(=O)OCC1=CC=CC=C1	1495.3	Standard non polar	33892256
Benzyl acetoacetate	CC(=O)CC(=O)OCC1=CC=CC=C1	1498.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Benzyl acetoacetate,1TMS,isomer #1	CC(=CC(=O)OCC1=CC=CC=C1)O[Si](C)(C)C	1673.6	Semi standard non polar	33892256
Benzyl acetoacetate,1TMS,isomer #1	CC(=CC(=O)OCC1=CC=CC=C1)O[Si](C)(C)C	1657.3	Standard non polar	33892256
Benzyl acetoacetate,1TMS,isomer #2	C=C(CC(=O)OCC1=CC=CC=C1)O[Si](C)(C)C	1601.3	Semi standard non polar	33892256
Benzyl acetoacetate,1TMS,isomer #2	C=C(CC(=O)OCC1=CC=CC=C1)O[Si](C)(C)C	1634.7	Standard non polar	33892256
Benzyl acetoacetate,1TBDMS,isomer #1	CC(=CC(=O)OCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	1906.9	Semi standard non polar	33892256
Benzyl acetoacetate,1TBDMS,isomer #1	CC(=CC(=O)OCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	1876.4	Standard non polar	33892256
Benzyl acetoacetate,1TBDMS,isomer #2	C=C(CC(=O)OCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	1841.6	Semi standard non polar	33892256
Benzyl acetoacetate,1TBDMS,isomer #2	C=C(CC(=O)OCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	1847.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Benzyl acetoacetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-6bae91acee540f8cc0e1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzyl acetoacetate 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 acetoacetate 10V, Positive-QTOF	splash10-0006-6900000000-62344b70f470cc0b8555	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl acetoacetate 20V, Positive-QTOF	splash10-0006-9200000000-7087db0fa6a89c9745b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl acetoacetate 40V, Positive-QTOF	splash10-0006-9000000000-6ec67218d38ed2481990	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl acetoacetate 10V, Negative-QTOF	splash10-000x-6900000000-78a1a8a5cb37176be690	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl acetoacetate 20V, Negative-QTOF	splash10-0a59-9600000000-259f094ed1296b4195a7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl acetoacetate 40V, Negative-QTOF	splash10-0a59-9100000000-51de05abd2086f51e6d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl acetoacetate 10V, Negative-QTOF	splash10-0a6r-4900000000-114c2556c47b19ce6aa1	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl acetoacetate 20V, Negative-QTOF	splash10-0a6r-9600000000-a09250eafa922a1db02c	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl acetoacetate 40V, Negative-QTOF	splash10-004i-9000000000-23eb754ec9000138e5e7	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl acetoacetate 10V, Positive-QTOF	splash10-0006-9000000000-ac6092011a9b5b6dc473	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl acetoacetate 20V, Positive-QTOF	splash10-0006-9000000000-9adb5302299f76cca944	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl acetoacetate 40V, Positive-QTOF	splash10-00kf-9000000000-de95915310d7fa79867d	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

Not Available

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

FDB020198

KNApSAcK ID

Not Available

Chemspider ID

125497

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

142266

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1003511

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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

Showing metabocard for Benzyl acetoacetate (HMDB0040446)

MOL for HMDB0040446 (Benzyl acetoacetate)

3D MOL for HMDB0040446 (Benzyl acetoacetate)

3D SDF for HMDB0040446 (Benzyl acetoacetate)

3D-SDF for HMDB0040446 (Benzyl acetoacetate)

PDB for HMDB0040446 (Benzyl acetoacetate)

3D PDB for HMDB0040446 (Benzyl acetoacetate)

SMILES for HMDB0040446 (Benzyl acetoacetate)

INCHI for HMDB0040446 (Benzyl acetoacetate)

Structure for HMDB0040446 (Benzyl acetoacetate)

3D Structure for HMDB0040446 (Benzyl acetoacetate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra