Page last updated: 2024-12-05

isobutyric acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Isobutyric acid, also known as 2-methylpropanoic acid, is a branched-chain carboxylic acid with the formula (CH3)2CHCOOH. It is a colorless liquid with a pungent odor. Isobutyric acid is found naturally in various sources, including milk, cheese, and human sweat. It is also produced industrially through the oxidation of isobutyl alcohol. Isobutyric acid is used as a flavoring agent in food and beverages, as well as in the production of pharmaceuticals and other chemicals. It is also used as a solvent and a plasticizer. Isobutyric acid is a common component of human sweat, and its production is increased during physical activity. It is also a component of the scent of some animals, such as the skunk. Isobutyric acid is a relatively weak acid, with a pKa of 4.82. It is soluble in water and ethanol, but not in ether. Isobutyric acid is studied for its potential applications in various fields, including medicine, agriculture, and food science.'

isobutyric acid: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

isobutyric acid : A branched fatty acid comprising propanoic acid carrying a methyl branch at C-2. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID6590
CHEMBL ID108778
CHEBI ID16135
MeSH IDM0074033

Synonyms (113)

Synonym
gtpl1060
alpha-methylpropanoic acid
iso-c3h7cooh
2-methylpropionsaeure
2,2-dimethylacetic acid
alpha-isobutyric acid
alpha-methylpropionic acid
isobuttersaeure
iso-butyric acid
CHEBI:16135 ,
epa pesticide chemical code 101502
hsdb 5228
brn 0635770
tenox ibp-2
fema no. 2222
kyselina isomaselna [czech]
un2529
methylpropanoic acid, 2-
ai3-24260
nsc 62780
isobutyric acid (natural)
einecs 201-195-7
caswell no. 503aa
acetic acid, dimethyl-
.alpha.-methylpropionic acid
propionic acid, 2-methyl-
.alpha.-methylpropanoic acid
isobutanoic acid
cenex rp b2
wln: qvy1&1
nsc62780
tenox ebp 2
2-methylpropionic acid
nsc-62780
isopropylformic acid
propanoic acid, 2-methyl-
inchi=1/c4h8o2/c1-3(2)4(5)6/h3h,1-2h3,(h,5,6
2-methyl-propionic acid
ALQ ,
isobutyric acid
dimethylacetic acid
C02632
79-31-2
2-methylpropanoic acid
isobutanoate
isobutyric acid, 99%
isobutyric acid, >=99%, fcc, fg
isobutyric acid, natural, >=99%, fcc, fg
1IUP
DB02531
2-methyl-propanoic acid
LMFA01020071
AKOS000118733
isobutyric acid [un2529] [flammable liquid]
tenox ibp-2 grain pr.
BMSE000439
CHEMBL108778
methylpropanoic acid
I0103
NCGC00248957-01
2-methpropanoic acid
NCGC00258759-01
dtxsid4021636 ,
cas-79-31-2
tox21_201207
dtxcid601636
STL146521
ec 201-195-7
unii-8ll210o1u0
kyselina isomaselna
8ll210o1u0 ,
4-02-00-00843 (beilstein handbook reference)
FT-0625068
2-methylpropanoic acid [hsdb]
isobutyric acid [fcc]
isobutyric acid [inci]
isobutyric acid [mi]
isobutyric acid [fhfi]
isopropylformic-acid
isopropyl carboxylic acid
2-methyl propanoic acid
i-butyric acid
tenox ibp 2
methylpropionic acid
2-propanecarboxylic acid
un 2529
mfcd00002658
isobutyric-d6 acid
F2191-0099
isobutyric acid, certified reference material, tracecert(r)
isobutyric acid, analytical standard
isobutyric acid, puriss. p.a., >=99.5%
a-methylpropionate
a-methylpropanoic acid
a-methylpropanoate
alpha-methylpropionate
a-methylpropionic acid
alpha-methylpropanoate
dimethylacetate
Q415062
Z104473380
STR03465
BCP34521
2-methyl-d3-propionic-3,3,3-d3 acid;[2h6]-2-methylpropionic acid
EN300-19272
?isobutyric acid
propanoic-333-d3acid 2-methyl- (9ci)
acide isobutyrique
2-methyl-propionsaure
isobuttersaure
fema number: 2222
propane-2-carboxylic acid
acido isobutirico

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Sustained release formulations of arbaclofen placarbil demonstrated sustained R-baclofen exposure in dogs with bioavailability up to 68%."( Arbaclofen placarbil, a novel R-baclofen prodrug: improved absorption, distribution, metabolism, and elimination properties compared with R-baclofen.
Annamalai, T; Bao, Y; Bu, L; Cundy, KC; Dias, T; Gallop, MA; Gao, M; Koller, K; Lal, R; Ludwikow, M; Luo, W; Nguyen, S; Peng, G; Phan, T; Raillard, SP; Scheuerman, RA; Sukbuntherng, J; Tai, EH; Upadhyay, S; Warren, MS; Wu, QQ; Yan, H; Yao, F; Zamora, J, 2009
)
0.35

Dosage Studied

ExcerptRelevanceReference
" For both fatty acids there was a close parallelism between the dose-response curve for the inhibition of turnover of [3H]acetate from the histones and the increase in receptor levels."( Short chain fatty acids modulate nuclear receptor and extranuclear L-triiodothyronine levels in glial C6 cells by different mechanisms.
Aranda, A; Montiel, F; Ortiz-Caro, J; Pascual, A; Yusta, B, 1988
)
0.27
" Arbaclofen placarbil was efficiently absorbed and rapidly converted to R-baclofen after oral dosing in rats, dogs, and monkeys."( Arbaclofen placarbil, a novel R-baclofen prodrug: improved absorption, distribution, metabolism, and elimination properties compared with R-baclofen.
Annamalai, T; Bao, Y; Bu, L; Cundy, KC; Dias, T; Gallop, MA; Gao, M; Koller, K; Lal, R; Ludwikow, M; Luo, W; Nguyen, S; Peng, G; Phan, T; Raillard, SP; Scheuerman, RA; Sukbuntherng, J; Tai, EH; Upadhyay, S; Warren, MS; Wu, QQ; Yan, H; Yao, F; Zamora, J, 2009
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
volatile oil componentAny plant metabolite that is found naturally as a component of a volatile oil.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Daphnia magna metaboliteA Daphnia metabolite produced by the species Daphnia magna.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
branched-chain saturated fatty acidAny saturated fatty acid with a carbon side-chain or isopropyl termination.
methyl-branched fatty acidAny branched-chain fatty acid containing methyl branches only.
fatty acid 4:0Any saturated fatty acid containing 4 carbons.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, meta-Cleavage product hydrolasePseudomonas fluorescensKi2,900.00002,900.00002,900.00002,900.0000AID977610
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Free fatty acid receptor 3Rattus norvegicus (Norway rat)EC50 (µMol)30.00005.00005.00005.0000AID1341023
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID94977Effect of compound on erythroid differentiation of K562 cells was determined after a period of 3 days at concentration 4 mM1999Bioorganic & medicinal chemistry letters, Nov-01, Volume: 9, Issue:21
Induction of erythroid differentiation of human K562 cells by 3-O-acyl-1,2-O-isopropylidene-D-glucofuranose derivatives.
AID94985Effect of compound on erythroid differentiation of K562 cells was determined after a period of 7 days at concentration 4 mM1999Bioorganic & medicinal chemistry letters, Nov-01, Volume: 9, Issue:21
Induction of erythroid differentiation of human K562 cells by 3-O-acyl-1,2-O-isopropylidene-D-glucofuranose derivatives.
AID94989Effect of compound on erythroid differentiation of K562 cells was determined after a period of 9 days at concentration 4 mM1999Bioorganic & medicinal chemistry letters, Nov-01, Volume: 9, Issue:21
Induction of erythroid differentiation of human K562 cells by 3-O-acyl-1,2-O-isopropylidene-D-glucofuranose derivatives.
AID94981Effect of compound on erythroid differentiation of K562 cells was determined after a period of 5 days at concentration 4 mM1999Bioorganic & medicinal chemistry letters, Nov-01, Volume: 9, Issue:21
Induction of erythroid differentiation of human K562 cells by 3-O-acyl-1,2-O-isopropylidene-D-glucofuranose derivatives.
AID447578Inhibition of HDAC in human Hela cells nuclear extracts assessed as residual activity at 500 uM by fluorimetric assay2009Bioorganic & medicinal chemistry, Jul-15, Volume: 17, Issue:14
Molecular modifications on carboxylic acid derivatives as potent histone deacetylase inhibitors: Activity and docking studies.
AID1123304Cytotoxicity against HGPRTase-deficient mouse S49 cells assessed as growth inhibition at 1000 uM after 72 hrs by trypan blue exclusion assay1979Journal of medicinal chemistry, Jul, Volume: 22, Issue:7
2'-O-Acyl-6-thioinosine cyclic 3',5'-phosphates as prodrugs of thioinosinic acid.
AID95143Inhibition of cell growth against human myeloid leukemia K562(S) cells1999Bioorganic & medicinal chemistry letters, Nov-01, Volume: 9, Issue:21
Induction of erythroid differentiation of human K562 cells by 3-O-acyl-1,2-O-isopropylidene-D-glucofuranose derivatives.
AID94965Evaluated for erythroid induction of benzidine-positive K562 cells at concentration 3 mM1999Bioorganic & medicinal chemistry letters, Nov-01, Volume: 9, Issue:21
Induction of erythroid differentiation of human K562 cells by 3-O-acyl-1,2-O-isopropylidene-D-glucofuranose derivatives.
AID1345904Human FFA2 receptor (Free fatty acid receptors)2003The Journal of biological chemistry, Jul-11, Volume: 278, Issue:28
Functional characterization of human receptors for short chain fatty acids and their role in polymorphonuclear cell activation.
AID1345808Human FFA3 receptor (Free fatty acid receptors)2004Proceedings of the National Academy of Sciences of the United States of America, Jan-27, Volume: 101, Issue:4
Short-chain fatty acids stimulate leptin production in adipocytes through the G protein-coupled receptor GPR41.
AID1345808Human FFA3 receptor (Free fatty acid receptors)2003The Journal of biological chemistry, Mar-28, Volume: 278, Issue:13
The Orphan G protein-coupled receptors GPR41 and GPR43 are activated by propionate and other short chain carboxylic acids.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2002Protein science : a publication of the Protein Society, Sep, Volume: 11, Issue:9
Crystal structures of a meta-cleavage product hydrolase from Pseudomonas fluorescens IP01 (CumD) complexed with cleavage products.
AID1811Experimentally measured binding affinity data derived from PDB2002Protein science : a publication of the Protein Society, Sep, Volume: 11, Issue:9
Crystal structures of a meta-cleavage product hydrolase from Pseudomonas fluorescens IP01 (CumD) complexed with cleavage products.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (178)

TimeframeStudies, This Drug (%)All Drugs %
pre-199050 (28.09)18.7374
1990's25 (14.04)18.2507
2000's59 (33.15)29.6817
2010's32 (17.98)24.3611
2020's12 (6.74)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 62.91

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index62.91 (24.57)
Research Supply Index5.23 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index105.14 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (62.91)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (1.64%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other180 (98.36%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]