Altholactone

Base Information

• Chemical Name: Altholactone
• CAS No.: 65408-91-5
• Molecular Formula: C13H12O4
• Molecular Weight: 232.236
• European Community (EC) Number: 804-197-1
• DSSTox Substance ID: DTXSID90331855
• Nikkaji Number: J18.576K
• Wikidata: Q27106790
• Metabolomics Workbench ID: 69346
• ChEMBL ID: CHEMBL512401
• Mol file: 65408-91-5.mol

Synonyms:2-phenyl-3-hydroxy-6,7-dihydro-furano-pyrone;2-phenyl-3-hydroxy-6,7-dihydrofuranopyrone;altholactone

Chemical Property of Altholactone

Chemical Property:

• Vapor Pressure: 1.97E-10mmHg at 25°C
• Melting Point: 108-109 °C(Solv: ethanol (64-17-5); benzene (71-43-2))
• Boiling Point: 490.4°Cat760mmHg
• PKA: 12.82±0.40(Predicted)
• Flash Point: 196.1°C
• PSA: 55.76000
• Density: 1.336g/cm³
• LogP: 0.96900
• Storage Temp.: ?20°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 232.07355886
• Heavy Atom Count: 17
• Complexity: 332

Purity/Quality:

98% ^*data from raw suppliers

Altholactone ≥95% (LC/MS-ELSD) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2C(C3C(O2)C=CC(=O)O3)O
• Isomeric SMILES: C1=CC=C(C=C1)[C@@H]2[C@H]([C@H]3[C@@H](O2)C=CC(=O)O3)O

Technology Process of Altholactone

There total 141 articles about Altholactone 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: 98.0%

(2R,3R,3aR,7aS)-3-(benzyloxy)-2-phenyl-3,3a-dihydro-2H-furo[3,2-b]pyran-5(7aH)-one (181534-69-0) → goniothalenol (65408-91-5)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at 40 ℃;

DOI:10.1016/0040-4039(96)01085-4 DOI:10.1021/jo970725u

Reference yield: 96.0%

(2S,3R,4R,5R)-2-<(Z)-(ethoxycarbonyl)-ethenyl>-3,4-bis(methoxymethoxy)-5-phenyltetrahydrofuran (115978-61-5) → goniothalenol (65408-91-5)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 1h; Heating;

DOI:10.1246/bcsj.62.2328

Reference yield: 93.0%

(5S)-5-hydroxy-(6S)-6-((2S,3R)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one (302348-81-8) → (+)-7,8-di-epi-altholactone (124868-11-7,65408-91-5,114488-17-4,114488-19-6,120019-23-0,120019-27-4,124868-12-8)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1021/ol000179i

upstream raw materials:

(Z)-3-((2S,3S,4S,5R)-3,4-Dihydroxy-5-phenyl-tetrahydro-furan-2-yl)-acrylic acid

(Z)-3-((2S,3S,4S,5R)-3,4-Dihydroxy-5-phenyl-tetrahydro-furan-2-yl)-acrylic acid tert-butyl ester

C₂₈H₂₄O₇

(2S,3R,4R,5R)-2-<(Z)-(ethoxycarbonyl)-ethenyl>-3,4-bis(methoxymethoxy)-5-phenyltetrahydrofuran

Downstream raw materials:

(2S,3R)-3-Hydroxy-2-phenyl-2,3,3a,7a-tetrahydro-furo[3,2-b]pyran-5-one

6,7-dihydro-7-methoxy-altholactone

(-)-etharvensin

(R)-3-((2R,3S,4S,5R)-3,4-Dihydroxy-5-phenyl-tetrahydro-furan-2-yl)-3-methoxy-propionic acid methyl ester