Cannabis Compound Database: Showing Compound Card for Isobutyl acetate (CDB000695)

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Record Information

Version

1.0

Created at

2020-03-19 00:51:38 UTC

Updated at

2020-12-07 19:07:41 UTC

CannabisDB ID

CDB000695

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Isobutyl acetate

Description

Acetic acid-2-methyl-propyl ester or 2-methylpropyl acetate or 2-methylpropyl ethanoate, also known as isobutylacetate, 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). Isobutyl acetate is a clear, colorless liquid that is only slightly soluble in water (0.7 g/100 mL). Isobutyl acetate is produced from the esterification of isobutanol with acetic acid. Industrially, it is used as a solvent for lacquer and nitrocellulose. It is found naturally in many fruits such as raspberries and pears. Isobutyl aceteate has a sweet, apple, tropical, banana aroma and a similar fruity taste. At higher concentrations the odor can be unpleasant and may cause symptoms of central nervous system depression such as nausea, dizziness and headache. Isobutyl acetate has been detected, but not quantified in, several different fruits, such as muskmelons, sweet bay, asian pears, cocoa beans, figs, papaya and pineapple. This could make isobutyl acetate a potential biomarker for the consumption of these foods. Isobutyl acetate has also been found in Cannabis sativa (PMID: 6991645 , 26657499 ).

Structure

MOL SDF PDB SMILES InChI

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	Generator
Isobutylacetate	MeSH

Chemical Formula

C₆H₁₂O₂

Average Molecular Weight

116.16

Monoisotopic Molecular Weight

116.0837

IUPAC Name

2-methylpropyl acetate

Traditional Name

isobutyl acetate

CAS Registry Number

110-19-0

SMILES

CC(C)COC(C)=O

InChI Identifier

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

InChI Key

GJRQTCIYDGXPES-UHFFFAOYSA-N

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Indirect biological role:

Toxin

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	-98.85 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	6.3 mg/mL at 25 °C	Not Available
logP	1.78	Not Available

Predicted Properties

Property	Value	Source
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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Isobutyl acetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-f217b5e6b92235a1dd71	Spectrum
GC-MS	Isobutyl acetate, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-25cc25b3ba0651c0ba45	Spectrum
GC-MS	Isobutyl acetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-47909851abe2172156c6	Spectrum
GC-MS	Isobutyl acetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-32ed7cd25a7cd585255a	Spectrum
GC-MS	Isobutyl acetate, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-497069f05d541433b66e	Spectrum
GC-MS	Isobutyl acetate, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-49585f528507ace5b393	Spectrum
GC-MS	Isobutyl acetate, non-derivatized, GC-MS Spectrum	splash10-014i-1900000000-bb28c34b11812942773d	Spectrum
GC-MS	Isobutyl acetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-ef6ece5c35a5dd154ad5	Spectrum
GC-MS	Isobutyl acetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-f217b5e6b92235a1dd71	Spectrum
GC-MS	Isobutyl acetate, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-25cc25b3ba0651c0ba45	Spectrum
GC-MS	Isobutyl acetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-47909851abe2172156c6	Spectrum
GC-MS	Isobutyl acetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-32ed7cd25a7cd585255a	Spectrum
GC-MS	Isobutyl acetate, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-497069f05d541433b66e	Spectrum
GC-MS	Isobutyl acetate, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-49585f528507ace5b393	Spectrum
GC-MS	Isobutyl acetate, non-derivatized, GC-MS Spectrum	splash10-014i-1900000000-bb28c34b11812942773d	Spectrum
GC-MS	Isobutyl acetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-ef6ece5c35a5dd154ad5	Spectrum
Predicted GC-MS	Isobutyl acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-df6cefc23abcd1e80417	Spectrum
Predicted GC-MS	Isobutyl acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-066r-9700000000-a748f357862b1b998434	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9100000000-edefa0d353dff24eb16b	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-f40694d799cd17a2cec4	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-7900000000-6534ebe4a3a380503d44	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aor-9200000000-fd7dc8a883948134a340	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-e0b525315cc093f0fd0c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-6eb8c377976b6fa47cd1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-9000000000-75ca9d459a88c83adee2	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-4531d1e7d918cb3881e5	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0600-9200000000-9d3e1ac44fb825b68474	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-c01bbbf5bed889264ddb	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-e19c8390ed8f55d45a2d	2021-09-24	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Taste receptor type 1 member 3	TAS1R3	1p36.33	Q7RTX0	details
Taste receptor type 1 member 2	TAS1R2	1p36.13	Q8TE23	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

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

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Showing Compound Card for Isobutyl acetate (CDB000695)

Structure for CDB000695 (Isobutyl acetate)