4-Acetylbutyric acid

Base Information

• Chemical Name: 4-Acetylbutyric acid
• CAS No.: 3128-06-1
• Molecular Formula: C6H10O3
• Molecular Weight: 130.144
• Hs Code.: 29183000
• European Community (EC) Number: 221-511-7
• NSC Number: 5281
• UNII: RO0W8YUJ2W
• DSSTox Substance ID: DTXSID9062855
• Nikkaji Number: J56.059F
• Wikipedia: 4-acetylbutyric acid
• Wikidata: Q27098282
• Metabolomics Workbench ID: 1534
• Mol file: 3128-06-1.mol

Synonyms:4-Acetylbutyric acid;5-OXOHEXANOIC ACID;3128-06-1;5-Ketohexanoic acid;Hexanoic acid, 5-oxo-;5-Ketocaproic acid;5-Oxohexanoate;5-oxo-hexanoic acid;5-oxocaproic acid;5-keto-n-caproic acid;delta-Oxocaproic acid;delta-Ketocaproic acid;4-acetyl-butyric acid;Glurate;gamma-Acetylbutyric acid;.delta.-Oxocaproic acid;.delta.-Ketocaproic acid;.gamma.-Acetylbutyric acid;4-acetyl-butanoic acid;4-Acetylbutyric Acid-d5;RO0W8YUJ2W;NSC-5281;MFCD00004412;5-ketohexanoate;5-ketocaproate;31280-60-1;delta-oxocaproate;4-acetylbutyrate;delta-ketocaproate;gamma-Acetylbutyrate;4-Acetylbutyricacid;g-Acetylbutyrate;5-oxocaproate;4-Acetyl-butyrate;4-Acetyl-butanoate;5-oxo-caproic acid;5-keto-N-Caproate;g-Acetylbutyric acid;5-keto-hexanoic acid;gamme-Acetylbutyric acid;UNII-RO0W8YUJ2W;SCHEMBL15468;4-Acetylbutyric acid, 97%;4-oxopentane-1-carboxylic acid;DTXSID9062855;CHEBI:15888;.DELTA.-KETOHEXANOIC ACID;NSC5281;NSC 5281;CAPROIC ACID, .DELTA.-OXO-;EINECS 221-511-7;LMFA01060010;TD8115;AKOS001273158;CS-W001957;HY-W001957;5-oxohexanoic acid;4-Acetylbutyric Acid;AS-54714;SY015106;FT-0600819;K0014;EN300-23059;C02129;J-018356;Q27098282;Z147652222;6,7-DIMETHOXY-1,2,3,4-TETRAHYDROISOQUINOLINE-1-ACETICACID;4AT

Chemical Property of 4-Acetylbutyric acid

Chemical Property:

• Vapor Pressure: 0.00139mmHg at 25°C
• Melting Point: 13-14 °C
• Refractive Index: n20/D 1.4451(lit.)
• Boiling Point: 275.5 at 760 mmHg
• PKA: 4.63±0.10(Predicted)
• Flash Point: >110 °C
• PSA: 54.37000
• Density: 1.09 g/cm³
• LogP: 0.83030
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Slightly soluble in water, chloroform and methanol.
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 130.062994177
• Heavy Atom Count: 9
• Complexity: 118

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Acetylbutyric acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/38:Irritating to eyes and skin.
• Hazard Codes: R36/38:Irritating to eyes and skin.
• Statements: 36/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)CCCC(=O)O
• Uses: 4-Acetylbutyric acid is used in the synthesis of selective indomethacin analogues for AKR1C3 inhibition in the treatment of castrate-resistant prostate cancer. It is also used to prepare PARP inhibitors for the treatment of cancer. 4-Acetylbutyric acid may be used in the preparation of the following compounds:5-hydroxyhexanoic acid6-methyl1-3,4-dihydro-pyran-2-one, precursor for 5-acetyl-tetrahydro-2-(3H)-furanonesubstituted N-aminolactams(±)-5-methyl-δ-valerolactoneCrystal Structure of T.th. HB8 O-acetylserine sulfhydrylase Complexed with 4-Acetylbutyric acid

Technology Process of 4-Acetylbutyric acid

There total 156 articles about 4-Acetylbutyric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 44.0%

cellulose (9004-34-6) → furfural (98-01-1) + 5-hydroxymethyl-2-furfuraldehyde (67-47-0) + formic acid (64-18-6) + β-D-glucose (492-61-5) + 5-ketohexanoic acid (3128-06-1) + levoglucosan (498-07-7)

Guidance literature:

With sulfuric acid; In tetrahydrofuran; at 190 ℃; for 0.166667h; Solvent; Temperature; Time; Catalytic behavior;

DOI:10.1002/cctc.201402299

Reference yield: 19.0%

cotton → formic acid (64-18-6) + 5-ketohexanoic acid (3128-06-1)

Guidance literature:

With hydrogenchloride; In water; at 149.84 ℃; for 2h; Temperature; Autoclave;

DOI:10.1039/c4ra06246a

Reference yield: 13.0%

agarose → 5-hydroxymethyl-2-furfuraldehyde (67-47-0) + LACTIC ACID (849585-22-4,106989-11-1,26811-96-1,31587-11-8,26100-51-6) + 1,1-dihydroxyacetone (1186-47-6) + 5-ketohexanoic acid (3128-06-1) + Glyceraldehyde (56-82-6,367-47-5,26793-98-6)

Guidance literature:

With chromium chloride; at 200 ℃; for 0.5h;

DOI:10.1039/c3ra43293a

upstream raw materials:

glutaric anhydride,

methyl magnesium iodide

2-Methylcyclopentanone

diethyl 2-acetylglutarate

Downstream raw materials:

6-methoxy-2-hexanone

(2S,3R,8aS)-3,8a-Dimethyl-2-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one

(3R,8aS)-8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one

ethyl 3-methyl-1-oxo-2-cyclohexene-2-carboxylate

Refernces

• 1、 Albertson. "-". . p. 669. Retrieved 1948.
• 2、 Weingarten, Ronen,Rodriguez-Beuerman, Alexandra,Cao, Fei,Luterbacher, Jeremy S.,Alonso, David Martin,Dumesic, James A.,Huber, George W.. "Selective conversion of cellulose to hydroxymethylfurfural in polar aprotic solvents". . p. 2229 - 2234. Retrieved 2014.
• 3、 Wang, Yingxiong,Pedersen, Christian Marcus,Qiao, Yan,Deng, Tiansheng,Shi, Jing,Hou, Xianglin. "In situ NMR spectroscopy: Inulin biomass conversion in ZnCl2 molten salt hydrate medium - SnCl4 addition controls product distribution". . p. 439 - 443. Retrieved 2014.
• 4、 Chavanne,de Vogel. "-". . . Retrieved 1928.
• 5、 Shen, Yue,Sun, Jiankui,Yi, Yuxuan,Wang, Bo,Xu, Feng,Sun, Runcang. "5-Hydroxymethylfurfural and levulinic acid derived from monosaccharides dehydration promoted by InCl3 in aqueous medium". . p. 114 - 120. Retrieved 2014.
• 6、 Gürbüz, Elif I.,Gallo, Jean Marcel R.,Alonso, David Martin,Wettstein, Stephanie G.,Lim, Wee Y.,Dumesic, James A.. "Conversion of hemicellulose into furfural using solid acid catalysts in γ-valerolactone". . p. 1270 - 1274. Retrieved 2013.
• 7、 Alam, Md. Imteyaz,De, Sudipta,Singh, Bhagat,Saha, Basudeb,Abu-Omar, Mahdi M.. "Titanium hydrogenphosphate: An efficient dual acidic catalyst for 5-hydroxymethylfurfural (HMF) production". . p. 42 - 48. Retrieved 2014.
• 8、 Ordomsky, Vitaly V.,Van Der Schaaf, John,Schouten, Jaap C.,Nijhuis, T. Alexander. "Fructose dehydration to 5-hydroxymethylfurfural over solid acid catalysts in a biphasic system". . p. 1812 - 1819,8. Retrieved 2012.
• 9、 He, Tianyu,Chen, Dengfeng,Qian, Shencheng,Zheng, Yu,Huang, Shenlin. "Selective C-C Bond Cleavage of Cycloalkanones by NaNO2/HCl". . p. 6525 - 6529. Retrieved 2021/09/02.
• 10、 Abramov, Pavel A.,Carbó, Jorge J.,Chesalov, Yuriy A.,Eltsov, Ilia V.,Errington, R. John,Evtushok, Vasilii Yu.,Glazneva, Tatyana S.,Ivanchikova, Irina D.,Kholdeeva, Oxana A.,Maksimchuk, Nataliya V.,Maksimov, Gennadii M.,Poblet, Josep M.,Solé-Daura, Albert,Yanshole, Vadim V.,Zalomaeva, Olga V.. "Activation of H2O2over Zr(IV). Insights from Model Studies on Zr-Monosubstituted Lindqvist Tungstates". . p. 10589 - 10603. Retrieved 2021/09/02.