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427764

Sigma-Aldrich

Geranic acid

technical grade, 85%

Synonyme(s) :

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

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About This Item

Formule linéaire :
(CH3)2C=CHCH2CH2C(CH3)=CHCO2H
Numéro CAS:
459-80-3
Poids moléculaire :
168.23
Numéro Beilstein :
1763804
Numéro CE :
207-299-9
Numéro MDL:
MFCD00036493
Code UNSPSC :
12352100
ID de substance PubChem :
24866778
Nomenclature NACRES :
NA.22

Qualité

technical grade

Pureté

85%

Forme

liquid

Indice de réfraction

n20/D 1.484 (lit.)

Point d'ébullition

250 °C (lit.)

Densité

0.97 g/mL at 25 °C (lit.)

Chaîne SMILES 

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+

Clé InChI

ZHYZQXUYZJNEHD-VQHVLOKHSA-N

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Catégories apparentées

Description générale

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).

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H312,H315

Classification des risques

Acute Tox. 4 Dermal - Skin Irrit. 2

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

271.4 °F - closed cup

Point d'éclair (°C)

133 °C - closed cup

Équipement de protection individuelle

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

Certificats d'analyse (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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