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Ginkgoneolic acid

Ginkgoneolic acid structure

CAS No:
20261-38-5
Formula:
C20H32O3
Chemical Name:
Ginkgoneolic acid
Synonyms:
Benzoic acid,2-hydroxy-6-tridecyl-;Salicylic acid,6-tridecyl-;2-Hydroxy-6-tridecylbenzoic acid;6-n-Tridecylsalicylic acid;6-Tridecylsalicylic acid;Ginkgoneolic acid;Ginkgolic acid C13:0
Categories:
Biochemical Engineering > Plant Extracts

Description

Ginkgolic Acid (C13:0) is a natural anticariogenic agent in that it exhibits antimicrobial activity against S. mutans and suppresses the specific virulence factors associated with its cariogenicity.IC50 value: Inhibiting the biofilm formation of S. mutans (MBIC (50) = 4 μg/mL); reduced 1-day-developed biofilm of S. mutans by 50 % or more at low concentration (MBRC (50) = 32 μg/mL).Target:In vitro: Ginkgolic Acid (C13:0) inhibited not only the growth of S. mutans planktonic cells at minim

Solid

2-Hydroxy-6-tridecylbenzoic acid is a hydroxybenzoic acid. It derives from a salicylic acid.

Ginkgoneolic acid Basic Attributes

Molecular Weight：

320.47

Exact Mass：

320.47

DSSTox ID：

DTXSID10174105

HScode：

29163990

Characteristics

PSA：

57.5

XLogP3：

8.4

Appearance：

Solid

Density：

1.0±0.1 g/cm3

Melting Point：

85 - 86 °C

Boiling Point：

449.5°C at 760 mmHg

Flash Point：

239.8±21.9 °C

Refractive Index：

1.519

Water Solubility：

0.006004 mg/L @ 25 °C (est)

Storage Conditions：

2-8°C

Vapor Pressure：

7.26E-09mmHg at 25°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

Marks：

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

Drug Information

MeSH Entry Terms：

6-n-TDSCA

Ginkgoneolic acid Use and Manufacturing

An oven-dried 20 mL vial was charged with Ru-1 (3 mg, 5.00 μmol), 2 (131 mg, 0.50 mmol) and closed with a crimp cap. The vial was evacuated and backfilled three times with argon. 1-Hexene (3.50 mmol, 0.45 mL) and DCM (1 mL) were added simultaneously via syringe under an argon atmosphere. The continuous elimination of formed ethylene was performedby connecting the reaction vessel via an open system to an oil bubbler. The resulting mixture was stirred at 60 °C for 6 h. After the reaction was complete, methanol (0.5 mL) and activated charcoal (20.0 mg) were added. The vial was closed witha septum cap, penetrated with a cannula for pressure equilibration and placed into an autoclave. The system was purged twice with H2 (5 bar) and finally pressurized to 5 bar. The resulting mixture was stirred for 3 h at 50 °C. After cooling down to room temperature, the pressure was slowly released under constant stirring at 300 rpm. The reaction mixture was filtered through celite and the filter cake was washed with DCM (2 × 5 mL). The solvent was removed in vacuo and the residue was dissolved in pentane (5 mL) and stored in the freezer untilprecipitation of the solid. The precipitate was filtered and washed with cold pentane (2 × 5 mL), yielding the product 3 as colorless solid (120 mg, 72percent). CHN-elemental analysis calcd for C20H32O3: C, 74.9; H, 10.1; found: C, 74.8; H, 9.8;1H NMR (300 MHz, CDCl3) δ 10.98 (s, 1H), 7.38 (dd, J = 8.3, 7.6 Hz, 1H), 6.89 (dd, J = 8.3, 1.2 Hz, 1H), 6.79 (dd, J = 7.5, 1.1 Hz, 1H), 2.92–3.06 (m, 2H), 1.54–1.70 (m, 2H), 1.21–1.44(m, 20H), 0.84–0.93 (m, 3H) ppm; 13C NMR (75 MHz, CDCl3)δ 176.1, 163.6, 147.9, 135.5, 130.3, 122.8, 115.9, 110.4, 36.5, 32.0, 31.9, 29.8, 29.69, 29.68, 29.65, 29.6, 29.5, 29.4, 29.3, 22.7, 22.2, 14.1 ppm

Computed Properties

Molecular Weight:320.5
XLogP3:8.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:13
Exact Mass:320.23514488
Monoisotopic Mass:320.23514488
Topological Polar Surface Area:57.5
Heavy Atom Count:23
Complexity:303
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Guide of Ginkgoneolic acid

Description
Basic Attributes
Characteristics
Safety Information
Drug Information
Use and Manufacturing
Computed Properties
Recommended Suppliers
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