Ginkgolic acid

Synonym(s):(Z)-6-(Pentadec-8-enyl)-2-hydroxybenzoic acid, Histone Acetyltransferase Inhibitor VI, PCAF Inhibitor II, SUMOylation Inhibitor, HAT Inhibitor VI;Histone Acetyltransferase Inhibitor VI, PCAF Inhibitor II, SUMOylation Inhibitor, (Z)-6-(Pentadec-8-enyl)-2-hydroxybenzoic acid, HAT Inhibitor VI;InSolution

CAS NO.：22910-60-7
Empirical Formula: C22H34O3
Molecular Weight: 346.5
MDL number: MFCD03093717
EINECS: 200-683-7
SAFETY DATA SHEET (SDS)
Update Date: 2023-06-08 09:02:27

What is Ginkgolic acid?

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.

The Uses of Ginkgolic acid

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.

Definition

ChEBI:Ginkgoic acid is a hydroxybenzoic acid. It derives from a salicylic acid.

General Description

Ginkgolic acid C15:1 is an alkylphenol belonging to the class of ginkgolic acids isolated from Ginkgo biloba leaves. It also shows strong allergenic properties, with carcinogenic and mutagenic activity.

Biochem/physiol Actions

Cell permeable: yes

Properties of Ginkgolic acid

Melting point:	45～48℃
storage temp.	2-8°C
solubility	Chloroform (Slightly), Methanol (Slightly)
Boiling point:	221-223 °C(Press: 4 Torr)
Density	0.9148 g/cm3
form	White solid
pka	3.08±0.30(Predicted)
color	White to Off-White
CAS DataBase Reference	22910-60-7(CAS DataBase Reference)

Safety information for Ginkgolic acid

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H317:Sensitisation, Skin H413:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P272:Contaminated work clothing should not be allowed out of the workplace. P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P333+P313:IF SKIN irritation or rash occurs: Get medical advice/attention.