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427764

Sigma-Aldrich

Geranic acid

technical grade, 85%

Synonym(s):

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

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About This Item

Linear Formula:
(CH3)2C=CHCH2CH2C(CH3)=CHCO2H
CAS Number:
459-80-3
Molecular Weight:
168.23
Beilstein:
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

Signal Word

Warning

Hazard Statements

H312,H315

Hazard Classifications

Acute Tox. 4 Dermal - Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

271.4 °F - closed cup

Flash Point(C)

133 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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On the constituents of a Chinese rose oil.
Ohno Y and Tanaka S.
Agricultural and Biological Chemistry, 41(2), 399-401 (1977)
Monitoring tea fermentation/manufacturing by direct analysis in real time (DART) mass spectrometry.
Fraser K, et al.
Food Chemistry, 141(3), 2060-2065 (2013)
W A Wolken et al.
Applied microbiology and biotechnology, 57(5-6), 731-737 (2002-01-10)
Spores of Penicillium digitatum ATCC 201167 transform geraniol, nerol, citral, and geranic acid into methylheptenone. Spore extracts of P. digitatum convert geraniol and nerol NAD+-dependently into citral. Spore extract also converts citral NAD+-dependently into geranic acid. Furthermore, a novel enzymatic
Jean Michel Brunel et al.
Bioorganic & medicinal chemistry, 21(5), 1174-1179 (2013-01-29)
Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate reagent (BOP) serves as an efficient and versatile coupling reagent for the design and synthesis of new polyamino geranic acid derivatives in moderate to good chemical yields varying from 47% to 83%. These compounds induced a significant decrease
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
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