Not to be confused with Germanic acid.
Geranic acid
Skeletal formula of geranic acid
Ball-and-stick model of the geranic acid molecule
Names
Preferred IUPAC name
(2E)-3,7-Dimethylocta-2,6-dienoic acid
Other names
Geranic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C10H16O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,7H,4,6H2,1-3H3,(H,11,12)/b9-7+ checkY
    Key: ZHYZQXUYZJNEHD-VQHVLOKHSA-N checkY
  • O=C(O)/C=C(/CC\C=C(/C)C)C
Properties
C10H16O2
Molar mass 168.236 g·mol−1
Appearance Oily liquid
Density 0.97 g/cm3
Boiling point 249 to 251 °C (480 to 484 °F; 522 to 524 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 133 °C (271 °F; 406 K)
Lethal dose or concentration (LD, LC):
3700 mg/kg (oral, rat)
Safety data sheet (SDS) Fisher Scientific
Related compounds
Related acids
 Nerolic acid, Octanoic acid
Related compounds
 Geraniol
Geranial
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Geranic acid, or 3,7-dimethyl-2,6-octadienoic acid, is a pheromone used by some organisms.[1] It is a double bond isomer of nerolic acid.

Pharmacology

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Choline geranate (also described as Choline And Geranic acid, or CAGE) has been developed as a novel biocompatible antiseptic material capable of penetrating skin and aiding the transdermal delivery of co-administered antibiotics.

The antibacterial properties of CAGE were analyzed against 24 and 72 hour old biofilms of 11 clinically isolated ESKAPE pathogens (defined as Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumanii, Pseudomonas aeruginosa, and Enterobacter sp, respectively), including multidrug resistant (MDR) isolates.

CAGE was observed to eradicate in vitro biofilms at concentrations as low as 3.56 mM (0.156% v:v) in as little as 2 hours, which represents both an improved potency and rate of biofilm eradication relative to that reported for most common standard-of-care topical antiseptics in current use. In vitro time-kill studies on 24 hour old Staphylococcus aureus biofilms indicate that CAGE exerts its antibacterial effect upon contact and a 0.1% v:v solution reduced biofilm viability by over three orders of magnitude (a 3log10 reduction) in 15 minutes.

Furthermore, disruption of the protective layer of exopolymeric substances in mature biofilms of Staphylococcus aureus by CAGE (0.1% v:v) was observed in 120 minutes. Insight into the mechanism of action of CAGE was provided with molecular modeling studies alongside in vitro antibiofilm assays. The geranate ion and geranic acid components of CAGE are predicted to act in concert to integrate into bacterial membranes, affect membrane thinning and perturb membrane homeostasis.[2]

References

edit
  1. ^ Geranic acid, pherobase.com
  2. ^ Greene, J. R.; Merrett, K. L.; Heyert, A. J.; Simmons, L. F.; Migliori, C. M.; Vogt, K. C.; Castro, R. S.; Phillips, P. D.; Baker, J. L.; Lindberg, G. E.; Fox, D. T.; Del Sesto, R. E.; Koppisch, A. T. (2019). "Scope and efficacy of the broad-spectrum topical antiseptic choline geranate". PLOS ONE. 14 (9) e0222211. Bibcode:2019PLoSO..1422211G. doi:10.1371/journal.pone.0222211. PMC 6748422. PMID 31527873.
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Nasonov pheromone

number of different terpenoids including geraniol, nerolic acid, citral and geranic acid. Bees use these to find the entrance to their colony or hive

Chrysanthemic acid

Harro J.; Jongsma, Maarten A. (2011-07-01). "Metabolic engineering of geranic acid in maize to achieve fungal resistance is compromised by novel glycosylation

Nerolic acid

gland of honey-bees along with geraniol, geranic acid, citral, farnesol, and nerol. Of these, nerolic acid, geraniol, and farnesol are present in the

C10H16O2

Chrysanthemic acid trans-4,5-Epoxy-(E)-2-decenal Geranic acid Iridodial Iridomyrmecin Jasmine lactone Lineatin Massoia lactone Nepetalactol Nerolic acid This set

List of honey bee pheromones

includes a number of terpenoids including geraniol, nerolic acid, citral and geranic acid. Other pheromones produced by most honey bees include rectal

Anisomeles malabarica

essential oil from tops and flowers yields triterpenebetulinic acid, citral and geranic acid. First described in 1771, it was initially named Nepeta malabarica

Geranial dehydrogenase

the following chemical reaction geranial + NAD+     H2O H+ H2O H+   geranic acid + NADH   The enzyme does not act on neral, the Z-isomer of geranial.