Angelic acid

Base Information

• Chemical Name: Angelic acid
• CAS No.: 565-63-9
• Molecular Formula: C5H8O2
• Molecular Weight: 100.117
• Hs Code.: 29161900
• European Community (EC) Number: 209-284-2,236-167-3
• NSC Number: 96885
• UNII: 54U4ZPB36F
• DSSTox Substance ID: DTXSID80897430
• Nikkaji Number: J6.512I
• Wikipedia: Angelic_acid
• Wikidata: Q903353
• Metabolomics Workbench ID: 100
• ChEMBL ID: CHEMBL55941
• Mol file: 565-63-9.mol

Synonyms:Angelic acid;565-63-9;cis-2-Methyl-2-butenoic acid;2-Methylisocrotonic acid;(Z)-2-methylbut-2-enoic acid;(2Z)-2-methylbut-2-enoic acid;2-Butenoic acid, 2-methyl-, (Z)-;2-butenoic acid, 2-methyl-, (2Z)-;2-methyl-2Z-butenoic acid;Angelicasaeure;Angelikasaeure;acide angelique;acido angelico;(Z)-2-Methyl-2-butenoic Acid;(Z)-2-methylcrotonic acid;cis-2-dimethylcrotonic acid;Crotonic acid, 2-methyl-, (Z)-;UNII-54U4ZPB36F;alpha-methyl isocrotonic acid;54U4ZPB36F;CHEBI:36431;Z-2-methylcrotonic acid;EINECS 209-284-2;NSC 96885;NSC-96885;alpha-methylisocrotonic acid;Z-2-methyl-2-butenoic acid;cis-2,3-dimethylacrylic acid;2-Methyl-2-butenoic acid, cis;(2Z)-2-Methyl-2-butenoic acid;2,3-DIMETHYLACRYLIC ACID, (Z)-;Angelikasaure;MFCD00002654;13201-46-2;ANGELICACID;ANGELIC ACID [MI];2-methyl-cis-crotonic acid;2-Methyl-(Z)-Crotonic acid;CHEMBL55941;SCHEMBL133954;(z)-2,3-dimethylacrylic acid;2-Methylbut-2(cis)-enoic acid;2-Methyl-(Z)-2-Butenoic acid;(Z) CH3CH=C(CH3)COOH;DTXSID80897430;2-Methyl-(2Z)-2-butenoic acid;cis-alpha,beta-dimethylacrylic acid;AMY19230;BCP28215;HY-N6929;NSC96885;BBL012257;LMFA01020029;s3803;STL163578;2-Butenoic acid,2-methyl-, (2Z)-;AKOS003662964;CCG-266029;CS-W009553;AC-30733;VS-03252;Crotonic acid, 2-methyl-, (Z)- (8CI);A1136;CIS-.ALPHA.,.BETA.-DIMETHYLACRYLIC ACID;A869906;Q903353;Q-201832

Chemical Property of Angelic acid

Chemical Property:

• Appearance/Colour: colorless monoclinic, rod, needle or flake crystal
• Melting Point: 44ºC
• Refractive Index: nD47 1.4434
• Boiling Point: 198.5 °C at 760 mmHg
• PKA: pK (25°) 4.30
• Flash Point: 95.9 °C
• PSA: 37.30000
• Density: 1.01 g/cm³
• LogP: 1.03720
• Storage Temp.: Refrigerator
• Solubility.: almost transparency in Methanol
• Water Solubility.: slightly soluble in hot water
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 103

Purity/Quality:

≥98% ^*data from raw suppliers

Angelic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 34:
• Hazard Codes: 34:
• Statements: 34
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C(C)C(=O)O
• Isomeric SMILES: C/C=C(/C)\C(=O)O
• Uses: Flavoring extracts.

Technology Process of Angelic acid

There total 63 articles about Angelic 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: 97.0%

(Z)-2-Bromo-2-butene (3017-68-3) + diphenylmethylsilanecarboxylic acid (18414-58-9) → Angelic acid (565-63-9)

Guidance literature:

With lithium trimethylsilanolate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In 1,4-dioxane; at 80 ℃; for 16h; Glovebox;

DOI:10.1021/ol4003465

Reference yield: 90.0%

methyl angelate (5953-76-4) → Angelic acid (565-63-9)

Guidance literature:

With lithium hydroxide; In methanol; water; for 4h; Heating;

DOI:10.1002/anie.200351745

Reference yield: 88.0%

isobutyl (Z)-2-methylbut-2-enoate (7779-81-9) → Angelic acid (565-63-9)

Guidance literature:

With lithium hydroxide monohydrate; In methanol; water; for 4h; Inert atmosphere; Reflux;

DOI:10.1002/ejoc.201403622

upstream raw materials:

Tiglic acid

(Z)-2-Bromo-2-butene

(E)-3-bromo-2-methylbut-2-enoic acid

2-hydroxy-2-methylbutyric acid

Downstream raw materials:

Tiglic acid

methyl angelate

2-Methylbutanoic acid

2,3-dihydroxy-2-methylbutyric acid

Refernces

• 1、 Ookawa,Ikeya,Sugama,Taguchi,Maruno. "Dibenzocyclooctadiene lignans from Kadsura japonica". . p. 1187 - 1191. Retrieved 1995.
• 2、 Morikawa, Toshio,Matsuda, Hisashi,Li, Ning,Li, Xian,Yoshikawa, Masayuki. "Bioactive saponins and glycosides part 29. Acylated oleanane-type triterpene saponins: Theasaponins A6, A7, and B 5 from the seeds of Camellia sinensis". . p. 2342 - 2348. Retrieved 2007.
• 3、 Schmidt,E.. "". . . Retrieved 1886.
• 4、 Kir'yalov,Serkerov. "". . . Retrieved 1966.
• 5、 Frolova, Tatyana S.,Ganbaatar, Jamsranjav,Petrova, Tatyana N.,Pokrovskii, Andrey G.,Radnaeva, Larisa D.,Rybalova, Tatyana V.,Shults, Elvira E.,Taraskin, Vasilii V.,Urbagarova, Bayarma M.. "Chromones and coumarins from Saposhnikovia divaricata (Turcz.) Schischk. Growing in Buryatia and Mongolia and their cytotoxicity". . . Retrieved 2020/07/23.
• 6、 Hurst, Timothy E.,Deichert, Julie A.,Kapeniak, Lucas,Lee, Roland,Harris, Jesse,Jessop, Philip G.,Snieckus, Victor. "Sodium Methyl Carbonate as an Effective C1 Synthon. Synthesis of Carboxylic Acids, Benzophenones, and Unsymmetrical Ketones". supporting information. p. 3882 - 3885. Retrieved 2019/06/07.