Compounds > citronellic acid
Page last updated: 2024-12-05

citronellic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Citronellic acid is a monoterpenoid carboxylic acid found in various essential oils, particularly those from citronella grass, lemon balm, and lemongrass. It is a colorless liquid with a pleasant, citrus-like odor. The synthesis of citronellic acid can be achieved through various methods, including the oxidation of citronellal, a naturally occurring aldehyde found in essential oils. Citronellic acid exhibits antimicrobial, antifungal, and insecticidal properties, making it a valuable component in cosmetics, pharmaceuticals, and pesticides. Its antimicrobial activity has been attributed to its ability to disrupt bacterial cell membranes, while its insecticidal properties are thought to be due to its neurotoxic effects on insects. The study of citronellic acid is driven by its potential applications in various industries, including pharmaceuticals, cosmetics, and agriculture. Its natural origin and bioactivity make it an attractive alternative to synthetic pesticides and antibiotics. Further research aims to optimize its synthesis, understand its mechanism of action, and explore its potential for developing novel therapies and pest control strategies.'

citronellic acid: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

citronellic acid : A monounsaturated fatty acid that is oct-6-enoic acid carrying methyl groups at positions 3 and 7. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID10402
CHEMBL ID2288023
CHEBI ID80507
SCHEMBL ID193354
MeSH IDM0523579

Synonyms (51)

Synonym
4-02-00-01610 (beilstein handbook reference)
unii-1jjt408r87
1jjt408r87 ,
citronellic acid
6-octenoic acid, 3,7-dimethyl-
fema no. 3142
brn 1722960
einecs 207-939-7
rhodinolic acid
citronellate
502-47-6
3,7-dimethyl-6-octenoic acid, >=95%, fg
rhodinic acid
LMFA01020104
3,7-dimethyl-6-octenoic acid
citronellic acid, 98%
STK801994
C1708
57030-77-0
FT-0693158
3,7-dimethyloct-6-enoic acid
3,7-dimethyl-oct-6-enoic acid
cas-502-47-6
dtxcid9027106
tox21_302694
NCGC00256732-01
dtxsid1047106 ,
FT-0623964
FT-0634039
AKOS015894379
chebi:80507 ,
CHEMBL2288023
citronellic acid, (+/-)-
citronellic acid [inci]
citronellic acid [fhfi]
BBL027400
SCHEMBL193354
3(rs),7-dimethyl-6-octenoic acid
citronellicacid
mfcd00002728
3,7-dimethyl-6-octenoic acid, natural, 97%, fg
callitrol
fema 3142
FT-0772986
Q2182744
STR02820
D89451
SY267119
CS-0173714
EN300-111384
Z1255423445
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
flavouring agentA food additive that is used to added improve the taste or odour of a food.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
monoterpenoidAny terpenoid derived from a monoterpene. The term includes compounds in which the C10 skeleton of the parent monoterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl groups).
medium-chain fatty acidAny fatty acid with a chain length of between C6 and C12.
monounsaturated fatty acidAny fatty acid with one double or triple bond in the fatty acid chain and singly bonded carbon atoms in the rest of the chain. MUFAs have positive effects on the cardiovascular system, and in diabetes treatment.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (1)

PathwayProteinsCompounds
citronellol degradation112

Protein Targets (4)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
glucocorticoid receptor [Homo sapiens]Homo sapiens (human)Potency19.49620.000214.376460.0339AID720692
estrogen nuclear receptor alphaHomo sapiens (human)Potency21.87510.000229.305416,493.5996AID743075
peroxisome proliferator activated receptor gammaHomo sapiens (human)Potency48.97220.001019.414170.9645AID743191
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_aHomo sapiens (human)Potency68.58960.001723.839378.1014AID743083
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1112518Displacement of [3H]TBOB binding to GABA receptor in Musca domestica (house fly) heads homogenates assessed as [3H]TBOB binding at 500 uM incubated for 90 min by scintillation counting method2012Pest management science, Aug, Volume: 68, Issue:8
Quantitative structure-activity relationships of monoterpenoid binding activities to the housefly GABA receptor.
AID1112517Toxicity to Musca domestica (house fly) applied to pronotum assessed as compound level per fly causing insect mortality measured after 24 hr2012Pest management science, Aug, Volume: 68, Issue:8
Quantitative structure-activity relationships of monoterpenoid binding activities to the housefly GABA receptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (14.29)29.6817
2010's4 (57.14)24.3611
2020's2 (28.57)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.40

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index31.40 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index5.24 (4.65)
Search Engine Demand Index36.71 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (31.40)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (12.50%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (87.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
vanillin
Vanilla: A plant genus of the family ORCHIDACEAE that is the source of the familiar flavoring used in foods and medicines (FLAVORING AGENTS).		2.0710benzaldehydes;
monomethoxybenzene;
phenols		anti-inflammatory agent;
anticonvulsant;
antioxidant;
flavouring agent;
plant metabolite
menthol
Menthol: A monoterpene cyclohexanol produced from mint oils.		2.0710p-menthane monoterpenoid;
secondary alcohol		volatile oil component
1-anilino-8-naphthalenesulfonate
1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.		2.1710aminonaphthalene;
naphthalenesulfonic acid		fluorescent probe
eucalyptol
[no description available]		2.0710
methyl salicylate
methyl salicylate: used in over-the-counter liniments, ointments, lotions for relief of musculoskeletal aches and pains; has hemolytic effect on human & sheep erythrocytes; RN given refers to parent cpd; structure in Merck Index, 9th ed, #5990. methyl salicylate : A benzoate ester that is the methyl ester of salicylic acid.		2.0710benzoate ester;
methyl ester;
salicylates		flavouring agent;
insect attractant;
metabolite
safrole
Safrole: A member of the BENZODIOXOLES that is a constituent of several VOLATILE OILS, notably SASSAFRAS oil. It is a precursor in the synthesis of the insecticide PIPERONYL BUTOXIDE and the drug N-methyl-3,4-methylenedioxyamphetamine (MDMA).. safrole : A member of the class of benzodioxoles that is 1,3-benzodioxole which is substituted by an allyl group at position 5. It is found in several plants, including black pepper, cinnamon and nutmeg, and is present in several essential oils, notably that of sassafras. It has insecticidal properties and has been used as a topical antiseptic. Although not thought to pose a significant carcinogenic risk to humans, findings of weak carcinogenicity in rats have resulted in the banning of its (previously widespread) use in perfumes and soaps, and as a food additive.		2.0710benzodioxolesflavouring agent;
insecticide;
metabolite;
plant metabolite
linalool
linalool: RN given refers to parent cpd without isomeric designation; structure. linalool : A monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum.		2.0710monoterpenoid;
tertiary alcohol		antimicrobial agent;
fragrance;
plant metabolite;
volatile oil component
thymol
Thymol: A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent.. thymol : A phenol that is a natural monoterpene derivative of cymene.		2.0710monoterpenoid;
phenols		volatile oil component
4-cymene
4-cymene: structure. p-cymene : A monoterpene that is toluene substituted by an isopropyl group at position 4.		2.0710monoterpene;
toluenes		human urinary metabolite;
plant metabolite;
volatile oil component
citronellal
citronellal: aldehyde of citronellol; found in citronella oil. citronellal : A monoterpenoid, the main component of citronella oil which gives it its distinctive lemon aroma.		7.0410aldehyde;
monoterpenoid		antifungal agent;
metabolite
piperidine
[no description available]		2.0710azacycloalkane;
piperidines;
saturated organic heteromonocyclic parent;
secondary amine		base;
catalyst;
human metabolite;
non-polar solvent;
plant metabolite;
protic solvent;
reagent
piperonal
piperonal: has been used as a pediculicide; structure. piperonal : An arenecarbaldehyde that is 1,3-benzodioxole substituted by a formyl substituent at position 5. It has been isolated from Piper nigrum.		2.0710arenecarbaldehyde;
benzodioxoles		fragrance;
insect repellent;
plant metabolite
1,4-cineole
1,4-cineole: monoterpene; flavor component of lime Citrus medica L. var acida; structure given in first source. 1,4-cineole : An oxabicycloalkane consisting of p-menthane with an epoxy bridge across positions 1 and 4.		2.0710
carvacrol
carvacrol : A phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1).		2.0710botanical anti-fungal agent;
p-menthane monoterpenoid;
phenols		agrochemical;
antimicrobial agent;
flavouring agent;
TRPA1 channel agonist;
volatile oil component
gold
Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.		7.0410copper group element atom;
elemental gold
citronellal, (r)-isomer
(R)-(+)-citronellal : The (3R)-stereoisomer of 3,7-dimethyloct-6-enal (citronellal).		2.0710citronellal
caprylates
Caprylates: Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure.. octanoate : A straight-chain saturated fatty acid anion that is the conjugate base of octanoic acid (caprylic acid); believed to block adipogenesis.		4.3250fatty acid anion 8:0;
straight-chain saturated fatty acid anion		human metabolite;
Saccharomyces cerevisiae metabolite
camphora
camphora: a component of Guanxingao, a kind of traditional Chinese rubber electuary medicine which is able to either cure or guard against coronary heart disease and angina pectoris. (R)-camphor : The (R)- enantiomer of camphor.		2.0710camphor
(+)-limonene
(4R)-limonene : An optically active form of limonene having (4R)-configuration.		2.0710limoneneplant metabolite
pulegone
pulegone: component of peppermint oil; RN given refers to cpd without isomeric designation; structure in Merck. (+)-pulegone : The (5R)-enantiomer of p-menth-4(8)-en-3-one.		2.0710p-menth-4(8)-en-3-one
1-alpha-terpineol
(S)-(-)-alpha-terpineol : The (S)-enantiomer of alpha-terpineol.		2.0710alpha-terpineolplant metabolite
e-z cinnamic acid
cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid		2.0710cinnamic acidplant metabolite
decaprenoic acid
decaprenoic acid: synthetic isoprenoid; RN given refers to cpd without isomeric designation; structure given in first source		2.3110monoterpenoid
phosphatidylcholines
Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.		2.17101,2-diacyl-sn-glycero-3-phosphocholine
piperidines
Piperidines: A family of hexahydropyridines.		2.0710
ConditionIndicatedRelationship StrengthStudiesTrials