22910-60-7

Basic information

• Product Name: Ginkgolic acid
• Synonyms: C-17:1;GINKGOLIC ACID;ROMANICARDIC ACID;Ginkgolic;C10794;6-[(8Z)-Pentadecenyl]-salicylic acid;6-[(8Z)-Pentadecenyl]-salicylic acid, Ginkgolic acid I;2-Hydroxy-6-[(8Z)-8-pentadecenyl]benzoic acid
• CAS NO: 22910-60-7
• Molecular Formula: C₂₂H₃₄O₃
• Molecular Weight: 346.5
• Product Categories: Miscellaneous Natural Products
• Mol File: 22910-60-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 45～48℃
• Boiling Point: 492.095 °C at 760 mmHg
• Flash Point: 265.51 °C
• Appearance: /
• Density: 1.015 g/cm³
• Vapor Pressure: 6.09E-11mmHg at 25°C
• Refractive Index: 1.523
• Storage Temp.: -20C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 3.08±0.30(Predicted)
• CAS DataBase Reference: Ginkgolic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Ginkgolic acid(22910-60-7)
• EPA Substance Registry System: Ginkgolic acid(22910-60-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-26
• WGK Germany: 3
• Hazardous Substances Data: 22910-60-7(Hazardous Substances Data)

Usage

Description

Ginkgolic acid, a hydroxybenzoic acid derived from salicylic acid, is an alkylphenol belonging to the class of ginkgolic acids isolated from Ginkgo biloba leaves. It exhibits strong allergenic properties, along with carcinogenic and mutagenic activity. Ginkgolic acid is slightly toxic and is known to be an allergen, which has led to the recommendation of using only standardized extracts that minimize its content. Despite these properties, ginkgolic acid has shown activity against the tubercle bacillus and has been used in traditional medicine for various therapeutic applications.

Uses

Used in Analytical Chemistry:
Ginkgolic acid C15:1 is 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). It serves as an analytical reference standard for the quantification of the analyte in Ginkgo biloba plant extracts and dietary supplements using chromatography techniques.
Used in Pharmaceutical Applications:
Ginkgolic acid has been used in the treatment of peripheral arterial circulation problems such as arteriosclerotic angiopathy, post-thrombotic syndrome, diabetic vasoconstriction with gangrene and angina, intermittent claudication, and Raynaud's disease. Additionally, extracts of Ginkgo biloba leaves and fruit have been utilized in traditional medicine for their potential therapeutic applications, including the amelioration of dementia.
Used in Inhibiting SUMOylation:
Ginkgolic acid C15:1 has been found to inhibit SUMOylation in vitro (IC50 = 3 μM) and in cells without affecting protein ubiquitination. It directly binds the SUMO-activating enzyme E1, blocking the formation of the E1-SUMO intermediate, which may have implications in the development of cancer treatments.
Used in Cancer Research:
Ginkgolic acid C15:1 has demonstrated the ability to suppress the development of pancreatic cancer xenografts in mice, indicating its potential use in cancer research and therapeutic development.

Biochem/physiol Actions

Cell permeable: yes

InChI:InChI=1/C22H34O3/c1-3-4-5-6-9-14-19(15-10-7-8-13-18(2)23)20-16-11-12-17-21(20)22(24)25/h10-12,15-19,23H,3-9,13-14H2,1-2H3,(H,24,25)/b15-10+

Upstream product

• 114802-13-0 2-methoxy-6-(8-pentadecenyl)benzoic acid 
• 217449-17-7 ethyl 6-<8(Z)-pentadecenyl>salicylate 
• 50816-19-8 8-bromooctanol 
• 28598-82-5 1-bromo-8-chloro-octane 
• 114802-11-8 ethyl 6-(7-formylheptyl)-2-methoxybenzoate 
• 114802-12-9 ethyl 2-methoxy-6-[8(Z)-pentadecenyl]benzoate 
• 332011-41-3 11-chloro-2-undecynal 
• 332011-42-4 11-chloro-3-methoxy-2-undecenal 
• 332011-40-2 11-chloro-1,1-diethoxy-2-undecyne 
• 332011-44-6 ethyl 6-(8-chlorooctyl)-2-methoxybenzoate 
• 332011-43-5 ethyl 6-(8-chlorooctyl)salicylate 
• 332011-45-7 ethyl 6-(8-iodooctyl)-2-methoxybenzoate 
• 10160-25-5 7-bromo-1-(2-tetrahydropyranyloxy)heptane 
• 10160-24-4 7-bromoheptyl alcohol 

Downstream Products

• 16611-84-0 6-Pentadecylsalicylic Acid 
• 58682-65-8 ginkgolic acid methyl ester 
• 111-71-7 heptanal 
• 120826-74-6 methyl (Z)-2-methoxy-6-(pentadec-8-en-1-yl)benzoate 

Relevant articles and documents

Structure-inspired design of a sphingolipid mimic sphingosine-1-phosphate receptor agonist from a naturally occurring sphingomyelin synthase inhibitor

Ginkgolic acid obtained as a sphingomyelin synthase inhibitor from a plant extract library inspired the concept of sphingolipid mimics. Ginkgolic acid-derived N-acyl anilines and ginkgolic acid 2-phosphate (GA2P) respectively mimic ceramide and sphingosine 1-phosphate (S1P) in structure and function. The GA2P-induced phosphorylation of ERK and internalization of S1P receptor 1 (S1P1) indicated potent agonist activity. Docking studies revealed that GA2P adopts a similar binding conformation to the bound ligand ML5, which is a strong antagonist of S1P1.

Synthesis of anacardic acids, 6-[8(Z),11(Z)-pentadecadienyl]salicylic acid and 6-[8(Z),11(Z),14-pentadecatrienyl]salicylic acid

11-Chloro-3-methoxy-2-undecenal was synthesized from 8-bromooctanol, and an annelation reaction with this aldehyde and ethyl acetoacetate proceeded to give the ethyl 6-(8-chlorooctyl)salicylate. Ethyl 6-(8-chlorooctyl)salicylate was converted to ethyl 6-(7-formylheptyl)-2-methoxybenzoate through the iodide after protection of the phenolic hydroxyl group. Finally, the Wittig reaction with the aldehyde and triphenylphosphonium iodides in the presence of BuLi gave the methoxybenzoates, and then treatments of these methoxybenzoates with BBr3 in CH2Cl2 and 10% NaOH in ethanol gave 6-[8(Z),11(Z)-pentadecadienyl]salicylic acid (anacardic acid 3) and 6-[8(Z),11(Z),14-pentadecatrienyl]salicylic acid (anacardic acid 4) which were isolated from plants of the anacardiaceae.

Synthesis of Anacardic Acids

The anacardic acids 1-11, isolated from various plants, were synthesized by a new general method.Reaction of the methyl alkynoates 12-18 with 1-methoxy-1,4-cyclohexadiene at 200 deg C afforded directly the methyl 2-methoxybenzoates 19-25 with long chain substituents in 6-position in 74-85percent yield.The dienophiles 12-16 were prepared by pyrolysis of the corresponding acylphosphoranes 26-30, the dienophiles 17 and 18 by methoxycarbonylation of the corresponding alkynes 31 and 32 via the hydroxy esters 33 and 34.Demethylation of 19-23 with AlI3 gave the methyl salicylates 35-39 which could be hydrolized to the anacardic acids 1-4 and 7.Hydrolysis of 24 and 25 provided the hydroxy acids 40 and 41, which were converted by treatment with CBr4/PPh3 into the acids 42 and 43 bearing bromoalkyl side chains.These were transformed into 44-47 by reaction with 1-hexynyllithium and 1-octynyllithium.Stereoselective hydrogenation of 44-47 gave 48-51 with (Z)-alkene side chains.In a similar approach 42 was converted into 52 and then into 53, which gave upon treatment with 1-pentynylmagnesium bromide or 1-heptynylmagnesium bromide the acids 54 and 55 with alkadiyne side chains.Stereoselective hydrogenation provided 56 and 57 with (Z,Z)-alkadiene side chains.The 2-methoxy group in 48-51, 56, 57 was demethylated by treatment with AlI3 to give the anacardic acids 5, 6, 8-11. - Keywords: Anacardic acids; Benzoates, methyl 6-alkyl-2-methoxy-; 2-Alkynoates, methyl; Aluminium triiodide, demethylation by treatment with