(9bR)-2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzo[b,d]furan-1,3(2H,9bH)-dione

Base Information

• Chemical Name: (9bR)-2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzo[b,d]furan-1,3(2H,9bH)-dione
• CAS No.: 7562-61-0
• Molecular Formula: C₁₈H₁₆O₇
• Molecular Weight: 344.321
• Hs Code.: 29329990
• Nikkaji Number: J136.433B
• ChEMBL ID: CHEMBL1450004
• Mol file: 7562-61-0.mol

Synonyms:(9bR)-2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzo[b,d]furan-1,3(2H,9bH)-dione;SR-01000781745;Usnone A;(-)-USNICACID;(+)-Usnic acid, 98%;MLS001173405;CHEMBL1450004;SCHEMBL14029303;HY-N0656A;HMS2859A03;NP341;BDBM50056923;AKOS024279833;NCGC00017160-02;NCGC00142398-01;(9aR)-4,8-diacetyl-1,3-dihydroxy-2,9a-dimethyl-7,9-dioxo-8,9a-dihydrobenzo[2,1 -d]benzo[b]furan;AC-34697;SMR000538904;CS-0007891;SR-01000781745-3;SR-01000781745-4;(9bR)-2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-dibenzofuran-1,3-dione

Chemical Property of (9bR)-2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzo[b,d]furan-1,3(2H,9bH)-dione

Chemical Property:

• Vapor Pressure: 3E-15mmHg at 25°C
• Melting Point: 201-203 °C(lit.)
• Refractive Index: 1.678
• Boiling Point: 594.8 °C at 760 mmHg
• PKA: 4.00±0.40(Predicted)
• Flash Point: 219.1 °C
• PSA: 121.13000
• Density: 1.49 g/cm³
• LogP: 2.12660
• Storage Temp.: 2-8°C
• Solubility.: almost transparency in Chloroform
• Water Solubility.: Partly soluble in water. Soluble in acetone, ethanol, chloroform and furfural.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 344.08960285
• Heavy Atom Count: 25
• Complexity: 708

Purity/Quality:

99% ^*data from raw suppliers

UsnicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(=C2C(=C1O)C3(C(=CC(=O)C(C3=O)C(=O)C)O2)C)C(=O)C)O
• Isomeric SMILES: CC1=C(C(=C2C(=C1O)[C@@]3(C(=CC(=O)C(C3=O)C(=O)C)O2)C)C(=O)C)O
• Uses: Usnic acid is used as fragrance; preservative in deodorants; in anti ac ne formulations; antibiotic for topical application. Usnic Acid acts as an antibacterial and antifungal agent, and are often seen used in cosmetics and facial application chemicals. (+)-Usnic acid has been used to study the following:The mechanism of its antimicrobial activity in bacterial cells.Its ability as an antibiofilm agent against Group A Streptococci (GAS).Its ability as a potent anti-virulent compound against Candida albicans.The mechanism of its toxic effect on hepatocytes.Its ability to inhibit the motility of human lung cancer cells.

Technology Process of (9bR)-2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzo[b,d]furan-1,3(2H,9bH)-dione

There total 8 articles about (9bR)-2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzo[b,d]furan-1,3(2H,9bH)-dione 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:

(-)-pseudoplacodiolic acid (72056-29-2) → (+)-usnic acid (15853-98-2,17669-01-1,56190-51-3,7562-61-0)

Guidance literature:

With hydrogenchloride; In methanol;

DOI:10.1016/0040-4039(81)80095-0

Reference yield:

usnic acid (15853-98-2,17669-01-1,56190-51-3,7562-61-0) → (+)-usnic acid (15853-98-2,17669-01-1,56190-51-3,7562-61-0)

Guidance literature:

ueber das Brucin-Salz;

Reference yield:

2,4,6-trihydroxy-3-methyl-acetophenon (2657-28-5) → usnic acid (15853-98-2,17669-01-1,56190-51-3,7562-61-0)

Guidance literature:

2,4,6-trihydroxy-3-methyl-acetophenon; With horseradish peroxidase type VI; dihydrogen peroxide; In methanol; at 37 ℃; pH=6.5; aq. phosphate buffer;

With sulfuric acid; acetic anhydride; at 40 ℃; for 0.5h;

DOI:10.1016/j.bmcl.2009.03.087

upstream raw materials:

usnic acid

(-)-pseudoplacodiolic acid

7,9-O,O-diacetylusnic acid

acetic acid

Downstream raw materials:

8-acetyl-5,7-dihydroxy-3,4a,6-trimethyl-1-phenyl-1,4a-dihydro-4H-benzofuro[3,2-f]indazol-4-one

2,6-diacetyl-3,7,9-trihydroxy-8,9b-dimethyl-4a,9b-dihydro-4H-dibenzofuran-1-one

(+)-usnic acid

usnic acid

Refernces

• 1、 Takahashi,Takani. "Usnic acid. XIV. The photo-oxidation of usnic acid". . p. 3585 - 3587. Retrieved 2007/10/08.