Compounds > 1,4-cineole
Page last updated: 2024-12-05

1,4-cineole

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

Description

1,4-Cineole, also known as eucalyptol, is a monoterpene oxide with a characteristic camphoraceous odor. It is a major component of eucalyptus oil and other essential oils. 1,4-Cineole is a naturally occurring compound found in various plants, including eucalyptus, rosemary, and tea tree. It has been studied for its potential medicinal properties, including antimicrobial, anti-inflammatory, and analgesic effects. 1,4-Cineole has also been investigated for its effects on respiratory health, particularly in the treatment of respiratory infections and asthma. It is commonly used in aromatherapy and as an ingredient in over-the-counter medications. The synthesis of 1,4-Cineole can be achieved through various chemical methods, including the oxidation of alpha-terpineol and the cyclization of limonene. 1,4-Cineole is a key ingredient in many commercial products, such as cough syrups, nasal sprays, and topical pain relievers. Its therapeutic potential has made it a subject of extensive scientific research. '

1,4-cineole: monoterpene; flavor component of lime Citrus medica L. var acida; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

1,4-cineole : An oxabicycloalkane consisting of p-menthane with an epoxy bridge across positions 1 and 4. [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]

FloraRankFlora DefinitionFamilyFamily Definition
Medicagenus[no description available]BignoniaceaeA plant family of the order Lamiales. The family is characterized by oppositely paired, usually compound leaves and bell- or funnel-shaped, bisexual flowers having a five-lobed calyx and corolla.[MeSH]
CitrusgenusA plant genus of the family RUTACEAE. They bear the familiar citrus fruits including oranges, grapefruit, lemons, and limes. There are many hybrids which makes the nomenclature confusing.[MeSH]RutaceaeA plant family in the order Sapindales that grows in warmer regions and has conspicuous flowers.[MeSH]
Citrus medicaspecies[no description available]RutaceaeA plant family in the order Sapindales that grows in warmer regions and has conspicuous flowers.[MeSH]

Cross-References

ID SourceID
PubMed CID10106
CHEMBL ID2288022
CHEBI ID80788
SCHEMBL ID231925
SCHEMBL ID13180469
SCHEMBL ID15450554
SCHEMBL ID18993155
MeSH IDM0164181

Synonyms (57)

Synonym
p-menthane, 1,4-epoxy
7-oxabicyclo[2.2.1]heptane, 1-methyl-4-(1-methylethyl)-
hsdb 5425
1,4-cineole (natural)
7-oxabicyclo(2.2.1)heptane, 1-methyl-4-(1-methylethyl)-
1-methyl-4-(1-methylethyl)-7-oxabicyclo(2.2.1)heptane
1-isopropyl-4-methyl-7-oxabicyclo(2.2.1)heptane
p-menthane, 1,4-epoxy-
einecs 207-428-9
1,4-epoxy-p-menthane
7-oxabicyclo(2.2.1)heptane, 1-isopropyl-4-methyl-
brn 0104974
fema no. 3658
1,4-cineol
1,4-cineole, >=85%
470-67-7
1,4-cineole
isocineole
1-methyl-4-propan-2-yl-7-oxabicyclo[2.2.1]heptane
C16909
unii-b55jtu839b
b55jtu839b ,
5-17-01-00273 (beilstein handbook reference)
1-isopropyl-4-methyl-7-oxabicyclo[2.2.1]heptane
CHEMBL2288022
chebi:80788 ,
S5419
1,4-cineole [fhfi]
1,4-epoxy-p-menthane [hsdb]
(+/-)-1,4-cineole
SCHEMBL231925
isocineple
1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane
1-methyl-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptane
(1s,4s)-1-methyl-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptane
4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptane
DTXSID3047396
SCHEMBL13180469
SCHEMBL15450554
1-isopropyl-4-methyl-7-oxabicyclo[2.2.1]heptane #
RFFOTVCVTJUTAD-UHFFFAOYSA-N
mfcd00209502
7-oxabicyclo(2.2.1)heptane, 1-isopropyl-4-methyl- (6ci)
1,4-cineole, analytical standard
1,4-cineole, >=95%, fg
SCHEMBL18993155
1-isopropyl-4-methylbicyclo[2.2.1]heptane
1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane, 9ci
HY-N7117
(1s,4s)-1-isopropyl-4-methyl-7-oxabicyclo[2.2.1]heptane
Q12470088
CCG-266250
CS-0066997
F82275
isocineoleisocineole
AS-81210
C3652

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"98 mg/adult) and was more toxic than either 1,4-cineole or nerolidol (LD₅₀ = 50."( Toxicity of Rhododendron anthopogonoides essential oil and its constituent compounds towards Sitophilus zeamais.
Deng, ZW; Du, SS; Liu, QZ; Liu, ZL; Wang, CF; Yang, K; Zhou, YX, 2011)		0.63
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (2)

Assay IDTitleYearJournalArticle
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (7.14)18.7374
1990's2 (14.29)18.2507
2000's1 (7.14)29.6817
2010's9 (64.29)24.3611
2020's1 (7.14)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 35.47

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index35.47 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index5.00 (4.65)
Search Engine Demand Index42.06 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (35.47)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
imidazole
imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.		1.9810imidazole
methylmercaptan
methylmercaptan: intermediate in the manufacturing of jet fuels, pesticides, fungicides, plastics, synthesis of methionine; odor may cause nausea; narcotic in high concentrations; depresses urea biosynthesis; RN given refers to parent cpd; structure		2.610alkanethiolhuman metabolite;
Saccharomyces cerevisiae metabolite
palmitic acid
Palmitic Acid: A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.. hexadecanoic acid : A straight-chain, sixteen-carbon, saturated long-chain fatty acid.		1.9910long-chain fatty acid;
straight-chain saturated fatty acid		algal metabolite;
Daphnia magna metabolite;
EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor;
plant metabolite
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.		2.7730p-menthane monoterpenoid;
secondary alcohol		volatile oil component
eucalyptol
[no description available]		2.9840
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
metyrapone
Metyrapone: An inhibitor of the enzyme STEROID 11-BETA-MONOOXYGENASE. It is used as a test of the feedback hypothalamic-pituitary mechanism in the diagnosis of CUSHING SYNDROME.. metyrapone : An aromatic ketone that is 3,3-dimethylbutan-2-one in which the methyl groups at positions 1 and 4 are replaced by pyridin-3-yl groups. A steroid 11beta-monooxygenase (EC 1.14.15.4) inhibitor, it is used in the diagnosis of adrenal insufficiency.		1.9810aromatic ketoneantimetabolite;
diagnostic agent;
EC 1.14.15.4 (steroid 11beta-monooxygenase) inhibitor
proadifen
Proadifen: An inhibitor of drug metabolism and CYTOCHROME P-450 ENZYME SYSTEM activity.		1.9810diarylmethane
propranolol
Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.		2.0610naphthalenes;
propanolamine;
secondary amine		anti-arrhythmia drug;
antihypertensive agent;
anxiolytic drug;
beta-adrenergic antagonist;
environmental contaminant;
human blood serum metabolite;
vasodilator agent;
xenobiotic
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
allyl isothiocyanate
allyl isothiocyanate: used in the manufacture of flavors, war gases; medical use as a counterirritant; structure. allyl isothiocyanate : An isothiocyanate with the formula CH2=CHCH2N=C=S. A colorless oil with boiling point 152degreeC, it is responsible for the pungent taste of mustard, horseradish, and wasabi.		2.0710alkenyl isothiocyanate;
isothiocyanate		antimicrobial agent;
antineoplastic agent;
apoptosis inducer;
lachrymator;
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
alpha-pinene
[no description available]		2.0510pineneplant metabolite
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.		2.4820monoterpenoid;
phenols		volatile oil component
carveol
carveol: structure given in first source; prolongs tumor latency and decreases tumor yield. carveol : A limonene monoterpenoid that is cyclohex-2-en-1-ol substituted by a methyl group at position 2 and a prop-1-en-2-yl group at position 5.		2.0810limonene monoterpenoidplant metabolite;
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
2-methylpentane
Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.		1.9810alkane
cyclohexanol
Cyclohexanols: Monohydroxy derivatives of cyclohexanes that contain the general formula R-C6H11O. They have a camphorlike odor and are used in making soaps, insecticides, germicides, dry cleaning, and plasticizers.. cyclohexanols : An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton.		2.4420cyclohexanols;
secondary alcohol		solvent
octylamine
octylamine: RN given refers to 1-octylamine. octan-1-amine : An 8-carbon primary aliphatic amine.		1.9810primary aliphatic aminemetabolite
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
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).		2.4820botanical anti-fungal agent;
p-menthane monoterpenoid;
phenols		agrochemical;
antimicrobial agent;
flavouring agent;
TRPA1 channel agonist;
volatile oil component
citronellic acid
citronellic acid: structure in first source. citronellic acid : A monounsaturated fatty acid that is oct-6-enoic acid carrying methyl groups at positions 3 and 7.		2.0710medium-chain fatty acid;
monoterpenoid;
monounsaturated fatty acid		flavouring agent;
plant metabolite
tri-n-octylamine
[no description available]		2.0510
alpha-terpineol
terpineol : A family of monoterpenols that have a p-menthane skeleton containing one double bond and bearing a single hydroxy substituent.		1.9910terpineolplant metabolite
limonene
Limonene: A naturally-occurring class of MONOTERPENES which occur as a clear colorless liquid at room temperature. Limonene is the major component in the oil of oranges which has many uses, including as flavor and fragrance. It is recognized as safe in food by the Food and Drug Administration (FDA).. limonene : A monoterpene that is cyclohex-1-ene substituted by a methyl group at position 1 and a prop-1-en-2-yl group at position 4 respectively.		2.0810cycloalkene;
p-menthadiene		human metabolite
menthone
menthone : The trans-stereoisomer of p-menthan-3-one.. (-)-menthone : A menthone that is cyclohexanone substituted by a methyl and an isopropyl group at positions 5 and 2 respectively (the 2S,5R-stereoisomer).		2.0810menthone
alkenes
[no description available]		2.0510
citronellal, (r)-isomer
(R)-(+)-citronellal : The (3R)-stereoisomer of 3,7-dimethyloct-6-enal (citronellal).		2.0710citronellal
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.		2.4820p-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
sesquiterpenes
[no description available]		2.0610
nerolidol
nerolidol: sesquiterpene; RN given refers to cpd without isomeric designation; nerol is also available. nerolidol : A farnesane sesquiterpenoid that is dodeca-1,6,10-triene which carries methyl groups at positions 3, 7 and 11 and a hydroxy group at position 3. It is a natural product that is present in various flowers and plants with a floral odor. Chemically, it exists in two geometric isomers, trans and cis forms. It is widely used in cosmetics (e.g. shampoos and perfumes), in non-cosmetic products (e.g. detergents and cleansers) and also as a food flavoring agent.. (6Z)-nerolidol : A nerolidol in which the double bond at position 6 adopts a cis-configuration.		2.0610nerolidol
nad
NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.		1.9810organophosphate oxoanioncofactor;
human metabolite;
hydrogen acceptor;
Saccharomyces cerevisiae metabolite
ConditionIndicatedRelationship StrengthStudiesTrials