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Details

Stereochemistry ACHIRAL
Molecular Formula C4H7O2.Na
Molecular Weight 110.0869
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Sodium butyrate

SMILES

[Na+].CCCC([O-])=O

InChI

InChIKey=MFBOGIVSZKQAPD-UHFFFAOYSA-M
InChI=1S/C4H8O2.Na/c1-2-3-4(5)6;/h2-3H2,1H3,(H,5,6);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C4H7O2
Molecular Weight 87.0972
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Butyric acid (butanoic acid) belongs to a group of short-chain fatty acids and is thought to play several beneficial roles in the gastrointestinal tract. The butyric anion is easily absorbed by enteric cells and used as a main source of energy. Moreover, butyric acid is an important regulator of colonocyte proliferation and apoptosis, gastrointestinal tract motility and bacterial microflora composition in addition to its involvement in many other processes including immunoregulation and anti-inflammatory activity. Butyric acid shows a protective effect in inflammatory response secondary to inflammatory bowel diseases. A beneficial effect of butyric acid as one constituent of a multifaceted mechanism modulating gastrointestinal function has also been stressed in patients with the stoma and coexisting constipation. Butyric acid supplementation combined with the use of probiotics should be adopted as one of the basic therapeutic strategies in this patient group, preceding treatment with laxatives. Sodium butyrate in the form of enemas (combined in a mixture with A-300 silicon dioxide) may be a successful method of therapeutic management in patients with radiation proctitis. Sodium butyrate may also prevent diarrhea through an increased passive absorption of water in the colon and its effects on the gut microflora.

Originator

Curator's Comment: Butyric acid was first observed in impure form in 1814 by the French chemist Michel Eugène Chevreul.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
9.0 µM [IC50]
12.0 µM [IC50]
15.0 µM [IC50]
16.0 µM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
Sodium butyrate induces transcription from the G alpha(i2) gene promoter through multiple Sp1 sites in the promoter and by activating the MEK-ERK signal transduction pathway.
2001-07-13
Characterization of the reaction mechanism for the XL-I form of bovine liver xenobiotic/medium-chain fatty acid:CoA ligase.
2001-07-01
Evidence for gene silencing in Haemophilus influenzae.
2001-07-01
Overexpression of Bcl-2 regulates sodium butyrate- and/or docetaxel-induced apoptosis in human bladder cancer cells both in vitro and in vivo.
2001-07-01
Evidence of a functional role for the cyclin-dependent kinase-inhibitor p21WAF1/CIP1/MDA6 in promoting differentiation and preventing mitochondrial dysfunction and apoptosis induced by sodium butyrate in human myelomonocytic leukemia cells (U937).
2001-07
HMG-CoA reductase inhibitor mevastatin enhances the growth inhibitory effect of butyrate in the colorectal carcinoma cell line Caco-2.
2001-07
Effect of temperature increase from 55 to 65 degrees C on performance and microbial population dynamics of an anaerobic reactor treating cattle manure.
2001-07
Genes modulated by histone acetylation as new effectors of butyrate activity.
2001-06-22
Evaluation of the activity and localization of 15-lipoxygenase-1 after introduction into human colorectal carcinoma Caco-2 cells.
2001-06-22
Purification of recombinant cutinase by extraction in an aqueous two-phase system facilitated by a fatty acid substrate.
2001-06-20
Olfactory response to mushroom composting emissions as a function of chemical concentration.
2001-06-13
Sodium butyrate induces growth inhibition and modulates galectin-8 expression in human lung carcinoma cells.
2001-06-09
p21 Waf1/Cip1 can protect human colon carcinoma cells against p53-dependent and p53-independent apoptosis induced by natural chemopreventive and therapeutic agents.
2001-06-07
p21 gene regulation during enterocyte differentiation.
2001-06-01
Inhibition of growth of methane-producing bacteria of the ruminant forestomach by hydroxymethylglutaryl-SCoA reductase inhibitors.
2001-06
Enhanced inducible mGlu1alpha receptor expression in Chinese hamster ovary cells.
2001-06
Aroma-active components of nonfat dry milk.
2001-06
Identification of new triarylethylene oxyalkanoic acid analogues as bone selective estrogen mimetics.
2001-06
Calmodulin-like skin protein: a new marker of keratinocyte differentiation.
2001-06
Effects of low levels of ciprofloxacin on a chemostat model of the human colonic microflora.
2001-06
Reduction of telomerase activity in human liver cancer cells by a histone deacetylase inhibitor.
2001-06
Intracellular pH regulation in colonocytes of rat proximal colon.
2001-05-31
Short-chain fatty acid derivatives stimulate cell proliferation and induce STAT-5 activation.
2001-05-15
[Microbiological processes in a high-temperature oil field].
2001-05-08
Comamonas nitrativorans sp. nov., a novel denitrifier isolated from a denitrifying reactor treating landfill leachate.
2001-05
Clostridium uliginosum sp. nov., a novel acid-tolerant, anaerobic bacterium with connecting filaments.
2001-05
A novel human suspension culture packaging cell line for production of high-titre retroviral vectors.
2001-05
Dietary inulin improves distal colitis induced by dextran sodium sulfate in the rat.
2001-05
The mechanism of propagation of intracellular calcium waves in cultured human uterine myocytes.
2001-05
Inhibition of the phosphatidylinositol 3-kinase pathway contributes to HT29 and Caco-2 intestinal cell differentiation.
2001-05
A bovine macrophage cell line supports bovine herpesvirus-4 persistent infection.
2001-05
Enhanced expression of mRNAs of antisecretory factor-1, gp96, DAD1 and CDC34 in human hepatocellular carcinomas.
2001-04-30
Enhanced maturation of porcine neonatal pancreatic cell clusters with growth factors fails to improve transplantation outcome.
2001-04-27
1,25-Dihydroxycholecalciferol enhances butyrate-induced p21(Waf1/Cip1) expression.
2001-04-27
Synergistic growth inhibition of prostate cancer cells by 1 alpha,25 Dihydroxyvitamin D(3) and its 19-nor-hexafluoride analogs in combination with either sodium butyrate or trichostatin A.
2001-04-05
Differential regulation of placental and germ cell alkaline phosphatases by glucocorticoid and sodium butyrate in human gastric carcinoma cell line TMK-1.
2001-04-01
Epstein-Barr virus latently infected cells are selectively deleted in simulated-microgravity cultures.
2001-04
Influence of isoform and DNP on butyrate transport across the sheep ruminal epithelium.
2001-04
Histone deacetylase inhibitors promote apoptosis and differential cell cycle arrest in anaplastic thyroid cancer cells.
2001-04
The influence of acetoacetate and butyrate on calcium influx and ATP concentrations in HT-29 cells.
2001-04
Comparison of fermentation of selected fructooligosaccharides and other fiber substrates by canine colonic microflora.
2001-04
Interleukin-18 enhances the production of interleukin-8 by eosinophils.
2001-04
Evaluation of the expression of NADPH oxidase components during maturation of HL-60 clone 15 cells to eosinophilic lineage.
2001-03
Dehalogenation of dichloroethene in a contaminated soil: fatty acids and alcohols as electron donors and an apparent requirement for tetrachloroethene.
2001-03
The role of the colonic flora in maintaining a healthy large bowel mucosa.
2001-03
Anthelmintic activity of the stem bark extracts of Berlina grandiflora and one of its active principles, Betulinic acid.
2001-03
Methotrexate stimulates lung fibroblasts and epithelial cells to release eosinophil chemotactic activity.
2001-03
Cloning and biochemical characterization of Co(2+)-activated bromoperoxidase-esterase (perhydrolase) from Pseudomonas putida IF-3 strain.
2001-02-09
Effect of the liquid upflow velocity on thermophilic sulphate reduction in acidifying granular sludge reactors.
2001-02
Downregulation of MLL-CBP fusion gene expression is associated with differentiation of SN-1 cells with t(11;16)(q23;p13).
2001-01-18
Patents

Sample Use Guides

Dietary Supplement: Sodium Butyrate 4.38 gms of sodium butyrate per day for 12 weeks
Route of Administration: Oral
A study by Zhang et al. analyzing human colorectal cancer cell lines (HCT-116 and HT-29) treated with sodium butyrate at concentrations ranging from 0.5–5 mM found that sodium butyrate inhibited the growth of the studied cancer cells, stimulated autophagy and induced apoptotic cell death.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:01:16 GMT 2025
Edited
by admin
on Mon Mar 31 18:01:16 GMT 2025
Record UNII
8RAS91C36W
Record Status Validated (UNII)
Record Version
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Name Type Language
NSC-174280
Preferred Name English
Sodium butyrate
HSDB   USP   USP-RS   WHO-DD  
Systematic Name English
SODIUM BUTYRATE [WHO-DD]
Common Name English
BUTYRIC ACID SODIUM SALT
Common Name English
SODIUM BUTYRATE [USP-RS]
Common Name English
SODIUM BUTYRATE [USP MONOGRAPH]
Common Name English
BUTYRIC ACID, SODIUM SALT
Common Name English
SODIUM BUTYRATE [HSDB]
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/05/284
Created by admin on Mon Mar 31 18:01:16 GMT 2025 , Edited by admin on Mon Mar 31 18:01:16 GMT 2025
DSLD 3740 (Number of products:1)
Created by admin on Mon Mar 31 18:01:16 GMT 2025 , Edited by admin on Mon Mar 31 18:01:16 GMT 2025
NCI_THESAURUS C1946
Created by admin on Mon Mar 31 18:01:16 GMT 2025 , Edited by admin on Mon Mar 31 18:01:16 GMT 2025
Code System Code Type Description
EVMPD
SUB25177
Created by admin on Mon Mar 31 18:01:16 GMT 2025 , Edited by admin on Mon Mar 31 18:01:16 GMT 2025
PRIMARY
HSDB
5655
Created by admin on Mon Mar 31 18:01:16 GMT 2025 , Edited by admin on Mon Mar 31 18:01:16 GMT 2025
PRIMARY
SMS_ID
100000089145
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PRIMARY
CHEBI
64103
Created by admin on Mon Mar 31 18:01:16 GMT 2025 , Edited by admin on Mon Mar 31 18:01:16 GMT 2025
PRIMARY
PUBCHEM
5222465
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PRIMARY
RS_ITEM_NUM
1613600
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PRIMARY
FDA UNII
8RAS91C36W
Created by admin on Mon Mar 31 18:01:16 GMT 2025 , Edited by admin on Mon Mar 31 18:01:16 GMT 2025
PRIMARY
CAS
156-54-7
Created by admin on Mon Mar 31 18:01:16 GMT 2025 , Edited by admin on Mon Mar 31 18:01:16 GMT 2025
PRIMARY
NSC
174280
Created by admin on Mon Mar 31 18:01:16 GMT 2025 , Edited by admin on Mon Mar 31 18:01:16 GMT 2025
PRIMARY
ChEMBL
CHEMBL62381
Created by admin on Mon Mar 31 18:01:16 GMT 2025 , Edited by admin on Mon Mar 31 18:01:16 GMT 2025
PRIMARY
WIKIPEDIA
SODIUM BUTYRATE
Created by admin on Mon Mar 31 18:01:16 GMT 2025 , Edited by admin on Mon Mar 31 18:01:16 GMT 2025
PRIMARY
NCI_THESAURUS
C2337
Created by admin on Mon Mar 31 18:01:16 GMT 2025 , Edited by admin on Mon Mar 31 18:01:16 GMT 2025
PRIMARY
ECHA (EC/EINECS)
205-857-6
Created by admin on Mon Mar 31 18:01:16 GMT 2025 , Edited by admin on Mon Mar 31 18:01:16 GMT 2025
PRIMARY
EPA CompTox
DTXSID3037672
Created by admin on Mon Mar 31 18:01:16 GMT 2025 , Edited by admin on Mon Mar 31 18:01:16 GMT 2025
PRIMARY
DRUG BANK
DBSALT002877
Created by admin on Mon Mar 31 18:01:16 GMT 2025 , Edited by admin on Mon Mar 31 18:01:16 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY