Ginkgolic acid

Base Information

• Chemical Name: Ginkgolic acid
• CAS No.: 22910-60-7
• Deprecated CAS: 480-48-8
• Molecular Formula: C22H34O3
• Molecular Weight: 346.51
• Hs Code.: 29182900
• European Community (EC) Number: 634-999-5
• ChEMBL ID: CHEMBL445177
• DSSTox Substance ID: DTXSID50872875
• Metabolomics Workbench ID: 70458
• Nikkaji Number: J15.322B
• Wikidata: Q1525050
• Mol file: 22910-60-7.mol

Synonyms:(Z)-2-Hydroxy-6-(8-pentadecenyl)benzoic acid;ginkgolic acid

Chemical Property of Ginkgolic acid

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 6.09E-11mmHg at 25°C
• Melting Point: 136-137oC
• Refractive Index: 1.523
• Boiling Point: 492.095 °C at 760 mmHg
• PKA: 3.08±0.30(Predicted)
• Flash Point: 265.51 °C
• PSA: 57.53000
• Density: 1.015 g/cm³
• LogP: 6.50010
• Storage Temp.: -20C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 8.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 346.25079494
• Heavy Atom Count: 25
• Complexity: 364

Purity/Quality:

more than 98% ^*data from raw suppliers

Ginkgolic acid C15:1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC=CCCCCCCCC1=C(C(=CC=C1)O)C(=O)O
• Isomeric SMILES: CCCCCC/C=C\CCCCCCCC1=C(C(=CC=C1)O)C(=O)O
• Description: Ginkgolic acid is slightly toxic and is an allergen; for this reason, some sources suggest using only the standardized extract, which is standardized to the flavonoids and minimizes ginkgolic acid content.Ginkgolic acid is active against the tubercle bacillus. Elsewhere, leaf extracts are used in peripheral arterial circulation problems like arteriosclerotic angiopathy, post-thrombotic syndrome, diabetic vasoconstriction with gangrene and angina, intermittent claudication，Raynaud's disease. Extracts are inhaled for ear, nose, and throat ailments like bronchitis and chronic rhinitis.Extracts of the leaves and fruit of Ginkgo plants have long been used in traditional medicine and have multiple potential therapeutic applications, including ameliorating dementia. However, ginkgolic acids, 2-hydroxy-6-alkylbenzoic acids related to anacardic acids, may be deleterious components in these extracts. Ginkgolic acid C15:1 is a 2-hydroxy-6-alkylbenzoic acid in which the alkyl chain contains 15 carbons and is unsaturated at the 8 position. It inhibits SUMOylation in vitro (IC50 = 3 μM) and in cells without affecting protein ubiquitination. Ginkgolic acid C15:1 directly binds the SUMO-activating enzyme E1, blocking the formation of the E1-SUMO intermediate. Ginkgolic acid C15:1 also suppresses the development of pancreatic cancer xenografts in mice.
• Uses: Ginkgolic acid C15:1 may be used as a reference standard in the quantitative determination of alkylphenols like ginkgolic acids in Ginkgolic extract using high performance liquid chromatography coupled with mass spectrometry(HPLC-MS).Ginkgolic acid C15:1 may be used as an analytical reference standard for the quantification of the analyte in Ginkgo biloba plant extracts, and dietary supplements using chromatography techniques.

Technology Process of Ginkgolic acid

There total 47 articles about Ginkgolic 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: 92.9%

ethyl 6-<8(Z)-pentadecenyl>salicylate (217449-17-7) → 6-(8-pentadecenyl)salicylic acid (22910-60-7)

Guidance literature:

With sodium hydroxide; In ethanol; for 2h; Heating;

DOI:10.1248/cpb.49.18

Reference yield: 80.0%

2-methoxy-6-(8-pentadecenyl)benzoic acid (114802-13-0) → 6-(8-pentadecenyl)salicylic acid (22910-60-7)

Guidance literature:

With aluminium(III) iodide; cyclohexene; In carbon disulfide; for 0.166667h; Heating;

Reference yield:

5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (154714-19-9) → 6-(8-pentadecenyl)salicylic acid (22910-60-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere; Schlenk technique

2.1: tetrabutyl-ammonium chloride; palladium diacetate; lithium chloride; lithium acetate / N,N-dimethyl acetamide / 3 h / 70 °C / Inert atmosphere; Schlenk technique; Sealed tube

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / Inert atmosphere; Schlenk technique

3.2: 1 h / -78 - 20 °C / Inert atmosphere; Schlenk technique

4.1: potassium hydroxide / water; 1,4-dioxane / 24 h / 55 °C / Inert atmosphere; Schlenk technique

With pyridine; n-butyllithium; lithium acetate; tetrabutyl-ammonium chloride; palladium diacetate; lithium chloride; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; N,N-dimethyl acetamide; water; 2.1: |Heck Reaction / 3.1: |Wittig Olefination / 3.2: |Wittig Olefination;

DOI:10.1021/acs.orglett.8b02705

upstream raw materials:

2-methoxy-6-(8-pentadecenyl)benzoic acid

ethyl 6-<8(Z)-pentadecenyl>salicylate

8-bromooctanol

1-bromo-8-chloro-octane

Downstream raw materials:

ginkgolic acid methyl ester

methyl (Z)-2-methoxy-6-(pentadec-8-en-1-yl)benzoate

6-Pentadecylsalicylic Acid

heptanal

Refernces

• 1、 Swamy, Mahadeva M. M.,Murai, Yuta,Ohno, Yusuke,Jojima, Keisuke,Kihara, Akio,Mitsutake, Susumu,Igarashi, Yasuyuki,Yu, Jian,Yao, Min,Suga, Yoshiko,Anetai, Masaki,Monde, Kenji. "Structure-inspired design of a sphingolipid mimic sphingosine-1-phosphate receptor agonist from a naturally occurring sphingomyelin synthase inhibitor". . p. 12758 - 12761. Retrieved 2018/12/01.
• 2、 Satoh, Mitsuru,Takeuchi, Naoki,Fujita, Takeshi,Yamazaki, Katsuya,Tobinaga, Seisho. "Synthesis of anacardic acids utilizing an annelation reaction of isoxazoles with ethyl acetoacetate". . p. 1501 - 1505. Retrieved 2007/10/03.