Hydrangeic acid

Base Information

• Chemical Name: Hydrangeic acid
• CAS No.: 491-79-2
• Molecular Formula: C₁₅H₁₂O₄
• Molecular Weight: 256.258
• UNII: GYE4WJ5J43
• DSSTox Substance ID: DTXSID201045314
• Nikkaji Number: J11.634C
• Wikipedia: Hydrangeic_acid
• Wikidata: Q15411033
• Metabolomics Workbench ID: 129404
• ChEMBL ID: CHEMBL248347
• Mol file: 491-79-2.mol

Synonyms:hydrangeic acid

Chemical Property of Hydrangeic acid

Chemical Property:

• XLogP3: 3.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 256.07355886
• Heavy Atom Count: 19
• Complexity: 331

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)O)C(=O)O)C=CC2=CC=C(C=C2)O
• Isomeric SMILES: C1=CC(=C(C(=C1)O)C(=O)O)/C=C/C2=CC=C(C=C2)O

Technology Process of Hydrangeic acid

There total 13 articles about Hydrangeic 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: 100.0%

hydrangenol (480-47-7) → Hydrangeaic acid (491-79-2,113428-99-2)

Guidance literature:

With potassium hydroxide; In methanol; for 1.5h; Heating;

DOI:10.1248/cpb.44.1890

Reference yield: 80.0%

(E)-4-(2-(2,2-dimethyl-4-oxo-4H-benzo[d] [1,3]dioxin-5-yl)vinyl)phenyl acetate → Hydrangeaic acid (491-79-2,113428-99-2)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; water; at 60 ℃; for 12h; Inert atmosphere;

DOI:10.1080/14786419.2016.1274891

Reference yield:

2-hydroxy-6-methylbenzoic acid (567-61-3) → Hydrangeaic acid (491-79-2,113428-99-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dmap; thionyl chloride / 1,2-dimethoxyethane / 3 h / 20 °C / Inert atmosphere

2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 20 h / 80 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

4.1: sodium tungstate (VI) dihydrate; dihydrogen peroxide / methanol / 12 h / 20 °C / Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.08 h / 0 °C / Inert atmosphere

5.2: 0 - 20 °C / Inert atmosphere

6.1: potassium hydroxide / water; tetrahydrofuran / 12 h / 60 °C / Inert atmosphere

With dmap; N-Bromosuccinimide; thionyl chloride; sodium tungstate (VI) dihydrate; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; sodium hydride; triethylamine; potassium hydroxide; In tetrahydrofuran; methanol; tetrachloromethane; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1080/14786419.2016.1274891

upstream raw materials:

hydrangenol

2-methyl-6-nitrobenzoic acid

2-hydroxy-6-methylbenzoic acid

2, 2, 5-trimethyl-4H-benzo[d][1,3]dioxin-4-one

Downstream raw materials:

lunularic acid

3,4'-bis-benzoyloxy-bibenzyl

lunularin

8-(tert-Butyl-dimethyl-silanyloxy)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-isochroman-1-one

Refernces

• 1、 -. "Compositions containing hypotriglyceridemically active stilbenoids". . . Retrieved 2008/06/13.
• 2、 Yoshikawa,Harada,Yagi,Okuno,Muraoka,Koyama,Murakami. "Chemical transformation from dihydroisocoumarin into benzylidene-phthalide by use of regiospecific oxidative lactonization mediated by copper chloride (H) - Syntheses of thunberginol F and hydramacrophyllol A and B". . p. 721 - 723. Retrieved 2007/10/02.