NP-MRD: Showing NP-Card for 2-Methylpropyl acetate (NP0001070)

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Record Information

Version

2.0

Created at

2012-09-11 17:41:50 UTC

Updated at

2021-08-19 23:58:44 UTC

NP-MRD ID

NP0001070

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Methylpropyl acetate

Description

2-Methylpropyl acetate, also known as isobutyl acetate, belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). The acetate ester of isobutanol. 2-Methylpropyl acetate is a sweet, apple, and banana tasting compound. 2-Methylpropyl acetate has been detected, but not quantified, in several different foods, such as rosemaries, figs, pineapples, cocoa beans, and asian pears.

Structure

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


  Mrv1652306242117433D          

 20 19  0  0  0  0            999 V2000
    3.1737   -0.6680    0.9002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9742   -0.0203    0.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9796    0.1988   -0.9639 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8603    0.3512    0.9822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2773    0.9604    0.4173 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9313    0.1062   -0.6354 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1340    0.8613   -1.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837   -1.1588    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2776   -1.7265    0.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1874   -0.5319    1.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0510   -0.0684    0.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0562    1.9550   -0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0284    1.1234    1.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2755   -0.1342   -1.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7312    0.1179   -1.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7581    1.2073   -0.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8228    1.6936   -1.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7216   -1.6992    0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2680   -0.8097    0.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0159   -1.7582   -0.7247 H   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  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  1  9  1  0  0  0  0
  1 10  1  0  0  0  0
  1 11  1  0  0  0  0
  5 12  1  0  0  0  0
  5 13  1  0  0  0  0
  6 14  1  0  0  0  0
  7 15  1  0  0  0  0
  7 16  1  0  0  0  0
  7 17  1  0  0  0  0
  8 18  1  0  0  0  0
  8 19  1  0  0  0  0
  8 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001070

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])([H])C(=O)OC([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O2/c1-5(2)4-8-6(3)7/h5H,4H2,1-3H3

> <INCHI_KEY>
GJRQTCIYDGXPES-UHFFFAOYSA-N

> <FORMULA>
C6H12O2

> <MOLECULAR_WEIGHT>
116.1583

> <EXACT_MASS>
116.083729628

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
13.110114105919525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylpropyl acetate

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
1.166851517666667

> <ALOGPS_LOGS>
-1.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.994378543053144

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
31.157000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isobutyl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       3.174  -0.668   0.900  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.974  -0.020   0.276  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.980   0.199  -0.964  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.860   0.351   0.982  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.277   0.960   0.417  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.931   0.106  -0.635  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.134   0.861  -1.166  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.484  -1.159   0.024  0.00  0.00           C+0
HETATM    9  H   UNK     0       3.278  -1.726   0.582  0.00  0.00           H+0
HETATM   10  H   UNK     0       3.187  -0.532   1.993  0.00  0.00           H+0
HETATM   11  H   UNK     0       4.051  -0.068   0.517  0.00  0.00           H+0
HETATM   12  H   UNK     0      -0.056   1.955  -0.018  0.00  0.00           H+0
HETATM   13  H   UNK     0      -1.028   1.123   1.216  0.00  0.00           H+0
HETATM   14  H   UNK     0      -0.276  -0.134  -1.485  0.00  0.00           H+0
HETATM   15  H   UNK     0      -2.731   0.118  -1.752  0.00  0.00           H+0
HETATM   16  H   UNK     0      -2.758   1.207  -0.321  0.00  0.00           H+0
HETATM   17  H   UNK     0      -1.823   1.694  -1.843  0.00  0.00           H+0
HETATM   18  H   UNK     0      -0.722  -1.699   0.596  0.00  0.00           H+0
HETATM   19  H   UNK     0      -2.268  -0.810   0.755  0.00  0.00           H+0
HETATM   20  H   UNK     0      -2.016  -1.758  -0.725  0.00  0.00           H+0
CONECT    1    2    9   10   11                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   12   13                                             
CONECT    6    5    7    8   14                                             
CONECT    7    6   15   16   17                                             
CONECT    8    6   18   19   20                                             
CONECT    9    1                                                            
CONECT   10    1                                                            
CONECT   11    1                                                            
CONECT   12    5                                                            
CONECT   13    5                                                            
CONECT   14    6                                                            
CONECT   15    7                                                            
CONECT   16    7                                                            
CONECT   17    7                                                            
CONECT   18    8                                                            
CONECT   19    8                                                            
CONECT   20    8                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol

Synonyms

Value	Source
2-Methyl-1-propyl acetate	ChEBI
2-Methylpropyl ethanoate	ChEBI
Acetate d'isobutyle	ChEBI
Acetic acid, 2-methylpropyl ester	ChEBI
Acetic acid, isobutyl ester	ChEBI
beta-Methylpropyl ethanoate	ChEBI
Essigsaeureisobutylester	ChEBI
I-butyl acetate	ChEBI
Isobutyl ethanoate	ChEBI
Isobutylacetat	ChEBI
Isobutylazetat	ChEBI
2-Methyl-1-propyl acetic acid	Generator
2-Methylpropyl ethanoic acid	Generator
Acetic acid d'isobutyle	Generator
Acetate, 2-methylpropyl ester	Generator
Acetate, isobutyl ester	Generator
b-Methylpropyl ethanoate	Generator
b-Methylpropyl ethanoic acid	Generator
beta-Methylpropyl ethanoic acid	Generator
Β-methylpropyl ethanoate	Generator
Β-methylpropyl ethanoic acid	Generator
I-butyl acetic acid	Generator
Isobutyl ethanoic acid	Generator
2-Methylpropyl acetic acid	Generator
2-Methyl-1-propanol, acetate	HMDB
2-Methylpropyl acetate, 9ci	HMDB
beta -Methylpropyl ethanoate	HMDB
FEMA 2175	HMDB
Isobutyl acetate	HMDB
Isobutyl acetate FCC	HMDB
Isobutyl acetate, 8ci	HMDB
Isobutylester kyseliny octove	HMDB
Isobutyl acetic acid	HMDB
Isobutylacetate	HMDB

Chemical Formula

C₆H₁₂O₂

Average Mass

116.1583 Da

Monoisotopic Mass

116.08373 Da

IUPAC Name

2-methylpropyl acetate

Traditional Name

isobutyl acetate

CAS Registry Number

110-19-0

SMILES

[H]C([H])([H])C(=O)OC([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C6H12O2/c1-5(2)4-8-6(3)7/h5H,4H2,1-3H3

InChI Key

GJRQTCIYDGXPES-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alpinia galanga	LOTUS Database	35616633
Ananas comosus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cannabis sativa	CannabisDB	Not Available
Carica papaya L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Coffea arabica	KNApSAcK Database	22123792
Cucumis melo	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ficus carica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Laurus nobilis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Malus pumila	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Oreotragus oreotragus	LOTUS Database	35616633
Psidium guajava	LOTUS Database	35616633
Pyrus communis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pyrus pyrifolia	FooDB	Gary R. Takeoka, Ron G. Buttery, and Robert A. Flath. Volatile Constituents of Asian Pear (Pyrus ...
Salvia rosmarinus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Theobroma cacao	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zanthoxylum schinifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Carboxylic acid esters

Alternative Parents

Substituents

Carboxylic acid ester
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

acetate ester (CHEBI:50569 )

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-98.85 °C	Not Available
Boiling Point	116.50 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	6.3 mg/mL at 25 °C	Not Available
LogP	1.78	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	7.71 g/L	ALOGPS
logP	1.74	ALOGPS
logP	1.17	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	31.16 m³·mol⁻¹	ChemAxon
Polarizability	13.11 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031246

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003275

KNApSAcK ID

C00050471

Chemspider ID

7747

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isobutyl_acetate

METLIN ID

Not Available

PubChem Compound

8038

PDB ID

Not Available

ChEBI ID

50569

Good Scents ID

rw1013631

References

General References

Yu H, Guo W, Xie T, Ai L, Tian H, Chen C: Aroma characteristics of traditional Huangjiu produced around Winter Solstice revealed by sensory evaluation, gas chromatography-mass spectrometry and gas chromatography-ion mobility spectrometry. Food Res Int. 2021 Jul;145:110421. doi: 10.1016/j.foodres.2021.110421. Epub 2021 May 19. [PubMed:34112423 ]
Yalage Don SM, Schmidtke LM, Gambetta JM, Steel CC: Aureobasidium pullulans volatilome identified by a novel, quantitative approach employing SPME-GC-MS, suppressed Botrytis cinerea and Alternaria alternata in vitro. Sci Rep. 2020 Mar 11;10(1):4498. doi: 10.1038/s41598-020-61471-8. [PubMed:32161291 ]
Lin MH, Ke LY, Yao DJ: Discrimination of Red Wines with a Gas-Sensor Array Based on a Surface-Acoustic-Wave Technique. Micromachines (Basel). 2019 Oct 26;10(11). pii: mi10110725. doi: 10.3390/mi10110725. [PubMed:31717824 ]
Conde-Martinez N, Sinuco DC, Osorio C: Chemical studies on curuba (Passiflora mollissima (Kunth) L. H. Bailey) fruit flavour. Food Chem. 2014 Aug 15;157:356-63. doi: 10.1016/j.foodchem.2014.02.056. Epub 2014 Feb 22. [PubMed:24679791 ]
Lytra G, Tempere S, Le Floch A, de Revel G, Barbe JC: Study of sensory interactions among red wine fruity esters in a model solution. J Agric Food Chem. 2013 Sep 11;61(36):8504-13. doi: 10.1021/jf4018405. Epub 2013 Aug 28. [PubMed:23984708 ]
Fernandez-Trujillo JP, Dos-Santos N, Martinez-Alcaraz R, Le Bleis I: Non-Destructive Assessment of Aroma Volatiles from a Climacteric Near-Isogenic Line of Melon Obtained by Headspace Stir-Bar Sorptive Extraction. Foods. 2013 Aug 28;2(3):401-414. doi: 10.3390/foods2030401. [PubMed:28239125 ]
Pang X, Guo X, Qin Z, Yao Y, Hu X, Wu J: Identification of aroma-active compounds in Jiashi muskmelon juice by GC-O-MS and OAV calculation. J Agric Food Chem. 2012 May 2;60(17):4179-85. doi: 10.1021/jf300149m. Epub 2012 Apr 20. [PubMed:22497266 ]
Ejiri S, Odo S, Takahashi H, Nishimura Y, Gotoh K, Nishihara Y, Takagi K: Negishi alkyl-aryl cross-coupling catalyzed by Rh: efficiency of novel tripodal 3-diphenylphosphino-2-(diphenylphosphino)methyl-2-methylpropyl acetate ligand. Org Lett. 2010 Apr 16;12(8):1692-5. doi: 10.1021/ol100210u. [PubMed:20225837 ]
Shine HJ, Zhao BJ, Marx JN, Ould-Ely T, Whitmire KH: Decomposition of alkene adducts of thianthrene cation radical in nitrile solvents. Formation of alkyl-2-oxazolines and a new class of four-component products: 5-[(1-alkoxyalkylidene)ammonio]alkylthianthrenium diperchlorates. J Org Chem. 2004 Dec 24;69(26):9255-61. doi: 10.1021/jo0402125. [PubMed:15609964 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing NP-Card for 2-Methylpropyl acetate (NP0001070)

MOL for NP0001070 (2-Methylpropyl acetate)

3D MOL for NP0001070 (2-Methylpropyl acetate)

3D SDF for NP0001070 (2-Methylpropyl acetate)

3D-SDF for NP0001070 (2-Methylpropyl acetate)

PDB for NP0001070 (2-Methylpropyl acetate)

3D PDB for NP0001070 (2-Methylpropyl acetate)

SMILES for NP0001070 (2-Methylpropyl acetate)

INCHI for NP0001070 (2-Methylpropyl acetate)

Structure for NP0001070 (2-Methylpropyl acetate)

3D Structure for NP0001070 (2-Methylpropyl acetate)