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427764

Sigma-Aldrich

Geranic acid

technical grade, 85%

Sinónimos:

3,7-Dimethyl-2,6-octadienoic acid

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About This Item

Fórmula lineal:
(CH3)2C=CHCH2CH2C(CH3)=CHCO2H
Número de CAS:
459-80-3
Peso molecular:
168.23
Beilstein/REAXYS Number:
1763804
EC Number:
207-299-9
MDL number:
MFCD00036493
UNSPSC Code:
12352100
PubChem Substance ID:
24866778
NACRES:
NA.22

grade

technical grade

assay

85%

form

liquid

refractive index

n20/D 1.484 (lit.)

bp

250 °C (lit.)

density

0.97 g/mL at 25 °C (lit.)

SMILES string

C\C(C)=C\CC\C(C)=C\C(O)=O

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+

InChI key

ZHYZQXUYZJNEHD-VQHVLOKHSA-N

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General description

Geranic acid is a polyunsaturated fatty acid. It is used as a bio-friendly cross-linker in the fabrication of a molecularly imprinted polymer. Geranic acid belongs to the terpenoid family. It exists as two stereoisomers with trans and cis geometry across the conjugated double bond.

Application

  • Enhancement of antibiotic properties: Capric acid and geranic acid were used to improve the pharmaceutical properties and antibacterial activity of levofloxacin (Alkhawaja et al., 2023).
  • Aryl hydrocarbon receptor modulation: Research on natural deep eutectic solvents including fatty acids like geranic acid has demonstrated their capability to modulate the aryl hydrocarbon receptor independently of traditional ligands, suggesting potential in metabolic regulation and therapeutic applications (Denis et al., 2023).
  • Transdermal delivery systems: A study on ionic liquids composed of geranic acid for obesity treatment highlighted their use in transdermal drug delivery systems, presenting a non-invasive alternative for therapeutic management (Lu et al., 2023).
  • Antimicrobial and antielastase properties: Geranic acid has been shown to inhibit elastase activity and bacterial growth, offering potential applications in oral health products and treatments for conditions involving pathogenic bacteria and inflammation (Laird et al., 2023).

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H312,H315

Hazard Classifications

Acute Tox. 4 Dermal - Skin Irrit. 2

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

271.4 °F - closed cup

flash_point_c

133 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificados de análisis (COA)

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Monitoring tea fermentation/manufacturing by direct analysis in real time (DART) mass spectrometry.
Fraser K, et al.
Food Chemistry, 141(3), 2060-2065 (2013)
U Heyen et al.
Applied and environmental microbiology, 66(7), 3004-3009 (2000-07-06)
Monoterpenes with an unsaturated hydrocarbon structure are mineralized anaerobically by the denitrifying beta-proteobacterium Alcaligenes defragrans. Organic acids occurring in cells of A. defragrans and culture medium were characterized to identify potential products of the monoterpene activation reaction. Geranic acid (E,E-3,7-dimethyl-2,6-octadienoic
D C Alexander et al.
Journal of bacteriology, 176(22), 7079-7084 (1994-11-01)
We report that rfe mutants of wild-type strains of Escherichia coli O7, O18, O75, and O111 did not express O-specific polysaccharide unless the rfe mutation was complemented by a cloned rfe gene supplied in a plasmid. The O polysaccharides in
Tanaya Chatterjee
Biotechnology and applied biochemistry, 39(Pt 3), 303-306 (2004-05-25)
Microbial degradation of geraniol, a natural monoterpene alcohol, was studied using a Rhodococcus sp. strain GR3 isolated from soil. The bioconversion product was identified as geranic acid [(2 E )-3,7-dimethylocta-2,6-dienoic acid] and its structure was established by (1)H-NMR, Fourier-transform IR
On the constituents of a Chinese rose oil.
Ohno Y and Tanaka S.
Agricultural and Biological Chemistry, 41(2), 399-401 (1977)
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