alpha-Angelica lactone

Base Information

• Chemical Name: alpha-Angelica lactone
• CAS No.: 591-12-8
• Molecular Formula: C5H6O2
• Molecular Weight: 98.1014
• Hs Code.: 29322090
• European Community (EC) Number: 209-701-8
• NSC Number: 654
• UNII: 29CRF6L9C5
• DSSTox Substance ID: DTXSID7047693
• Nikkaji Number: J13.666B
• Wikidata: Q15726097
• Metabolomics Workbench ID: 55367
• ChEMBL ID: CHEMBL478640
• Mol file: 591-12-8.mol

Synonyms:alpha-angelicalactone;angelica lactone;angelica lactone, (alpha)-isomer;angelica lactone, (beta)-isomer

Chemical Property of alpha-Angelica lactone

Chemical Property:

• Appearance/Colour: White crystalline with rich aroma of tonka beans and chocolate flavor
• Vapor Pressure: 0.023mmHg at 25°C
• Melting Point: 13-17 °C(lit.)
• Refractive Index: n20/D 1.448(lit.)
• Boiling Point: 249.412 °C at 760 mmHg
• PKA: pK1:4.3 (25°C)
• Flash Point: 68.333 °C
• PSA: 26.30000
• Density: 1.121 g/cm³
• LogP: 0.83710
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Ethyl Acetate
• Water Solubility.: 5 g/100 mL (25 ºC)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 98.036779430
• Heavy Atom Count: 7
• Complexity: 124

Purity/Quality:

99% ^*data from raw suppliers

5-Methylfuran-2(3H)-one ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CCC(=O)O1
• Uses: alpha-Angelicalactone acts as acancer chemopreventive agent. It is used in the synthesis of glutathione and the activity of glutathione-S-transferase and UDP-glucunonosyltransferase detoxification enzymes in esophagus, stomach, intestine, and liver. It is used in oral care formulations to round out mint notes and in coffee flavors.

Technology Process of alpha-Angelica lactone

There total 67 articles about alpha-Angelica lactone 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: 83.0%

α-D-fructofuranose (10489-79-9) → 5-methyl-2-furanone (591-12-8) + 5-hydroxy-5-methyl-dihydro-furan-2-one (53179-31-0) + 5-hydroxymethyl-2-furfuraldehyde (67-47-0) + β-D-glucose (492-61-5)

Guidance literature:

platinum(II) chloride; In 1-ethyl-3-methyl-1H-imidazol-3-ium chloride; at 80 ℃; for 3h; Product distribution / selectivity;

Reference yield: 64.0%

levulinic acid (123-76-2) → 5-methyl-5H-furan-2-one (591-11-7) + 5-methyl-2-furanone (591-12-8)

Guidance literature:

With H-ZSM₅/SiO₂; at 129.84 ℃; under 75.0075 Torr; Reagent/catalyst; Temperature;

DOI:10.1039/c4gc00501e

Reference yield: 60.0%

levulinic acid (123-76-2) → 5-methyl-2-furanone (591-12-8)

Guidance literature:

With phosphoric acid; Heating;

DOI:10.1055/s-2005-868506

upstream raw materials:

5-methyl-5H-furan-2-one

prop-2-yn-1-ylpropanedioic acid

4-pentynoic acid

zinc(II) carbonate

Downstream raw materials:

levulinic acid methyl ester

4,5-Dihydro-5-methoxy-5-methylfuran-2(3H)-one

3-((Ξ)-4-amino-benzylidene)-5-methyl-3H-furan-2-one

4,5-Dihydro-5-ethoxy-5-methylfuran-2(3H)-one

Refernces

• 1、 Cong, Yu,Li, Guangyi,Li, Ning,Wang, Aiqin,Wang, Ran,Wang, Xiaodong,Xu, Jilei,Zhang, Tao. "Synthesis of renewable alkylated naphthalenes with benzaldehyde and angelica lactone". supporting information. p. 5474 - 5480. Retrieved 2021/08/16.
• 2、 Yu, Chenguang,Ji, Peng,Zhang, Yueteng,Meng, Xiang,Wang, Wei. "Construction of Enantioenriched γ,γ-Disubstituted Butenolides Enabled by Chiral Amine and Lewis Acid Cascade Cocatalysis". supporting information. p. 7656 - 7660. Retrieved 2021/10/12.