| Identification | More | [Name]
Ginkgolic acid | [CAS]
22910-60-7 | [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
2-Hydroxy-6-[(Z)-8-pentadecenyl]benzoic acid
Anacardic acid monoene
Phenolic acid C15:1 | [EINECS(EC#)]
200-683-7 | [Molecular Formula]
C22H34O3 | [MDL Number]
MFCD03093717 | [Molecular Weight]
346.5 | [MOL File]
22910-60-7.mol |
| Chemical Properties | Back Directory | [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 | [InChI]
InChI=1S/C22H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h7-8,15,17-18,23H,2-6,9-14,16H2,1H3,(H,24,25)/b8-7- | [InChIKey]
YXHVCZZLWZYHSA-FPLPWBNLSA-N | [SMILES]
C(O)(=O)C1=C(CCCCCCC/C=C\CCCCCC)C=CC=C1O | [LogP]
9.269 (est) | [CAS DataBase Reference]
22910-60-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H317-H413 | [Precautionary statements ]
P261-P272-P273-P280-P302+P352-P333+P313 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3 | [HS Code ]
29182900 | [Storage Class]
10 - Combustible liquids |
| Hazard Information | Back Directory | [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. | [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 | [References]
[1] X HE. High-performance liquid chromatography-electrospray ionization-mass spectrometry study of ginkgolic acid in the leaves and fruits of the ginkgo tree (Ginkgo biloba).[J]. Journal of chromatographic science, 2000, 38 4: 169-173. DOI: 10.1093/chromsci/38.4.169
[2] ISAO FUKUDA. Ginkgolic acid inhibits protein SUMOylation by blocking formation of the E1-SUMO intermediate.[J]. Chemistry & biology, 2009, 16 2: 133-140. DOI: 10.1016/j.chembiol.2009.01.009
[3] HONG-BIN LUO. SUMOylation at K340 inhibits tau degradation through deregulating its phosphorylation and ubiquitination.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2014: 16586-16591. DOI: 10.1073/pnas.1417548111
[4] JIGUANG MA. Ginkgolic acid suppresses the development of pancreatic cancer by inhibiting pathways driving lipogenesis.[J]. Oncotarget, 2015: 20993-21003. DOI: 10.18632/oncotarget.3663 |
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