Record Information
Version1.0
Creation date2010-04-08 22:11:15 UTC
Update date2019-11-26 03:10:00 UTC
Primary IDFDB014416
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namealpha-Terpineol
DescriptionFlavouring agent Terpineol is a naturally occurring monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. There are three isomers, alpha-, beta-, and gamma-terpineol, the last two differing only by the location of the double bond. Terpineol is usually a mixture of these isomers with alpha-terpineol as the major constituent. alpha-Terpineol is found in many foods, some of which are cabbage, cardamom, fennel, and lemon grass.
CAS Number98-55-5
Structure
Thumb
Synonyms
SynonymSource
1-alpha-TerpineolChEBI
1-Menthene-8-olChEBI
1-Methyl-4-isopropyl-1-cyclohexen-8-olChEBI
1-Methyl-4-isopropyl-1-cyclohexene-8-olChEBI
2-(4-Methyl-3-cyclohexenyl)-2-propanolChEBI
alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanolChEBI
DL-alpha-TerpineolKegg
1-a-TerpineolGenerator
1-Α-terpineolGenerator
a,a,4-Trimethyl-3-cyclohexene-1-methanolGenerator
Α,α,4-trimethyl-3-cyclohexene-1-methanolGenerator
DL-a-TerpineolGenerator
DL-Α-terpineolGenerator
a-TerpineolGenerator
Α-terpineolGenerator
(+-)-alpha-Terpineolmanual
(1R)-a,a,4-Trimethyl-3-cyclohexene-1-methanolGenerator
(1R)-α,α,4-trimethyl-3-cyclohexene-1-methanolGenerator
(R)-(+)-a-TerpineolGenerator
(R)-(+)-α-terpineolGenerator
(R)-a-TerpineolGenerator
(R)-a,a,4-Trimethylcyclohex-3-ene-1-methanolGenerator
(R)-alpha-TerpineolChEBI
(R)-α-terpineolGenerator
(R)-α,α,4-trimethylcyclohex-3-ene-1-methanolGenerator
α-Terpineolbiospider
α,α,4-Trimethyl-3-Cyclohexene-1-methanolbiospider
2-(4-Methyl-3-cyclohexen-1-yl)-2-propanolbiospider
2-(4-Methylcyclohex-3-en-1-yl)propan-2-olbiospider
2-(4-Methylcyclohex-3-enyl)propan-2-ol (alpha-terpineol)HMDB
3-Cyclohexene-1-methanol, α,α4-trimethyl-biospider
3-Cyclohexene-1-methanol, alpha,alpha,4-trimethyl-biospider
a,a,4-Trimethyl-3-cyclohexene-1-methanol, 9CIdb_source
alpha-TerpinenolHMDB
alpha-Terpineolbiospider
alpha-TerpineoleHMDB
alpha-TerpinolHMDB
alpha,alpha,4-Trimethyl-3-Cyclohexene-1-methanolbiospider
FEMA 3045db_source
Lily OF valleyHMDB
Menth-1-en-8-olbiospider
TerpenolHMDB
TerpineolHMDB
Terpineol schlechthinHMDB
Predicted Properties
PropertyValueSource
logP2.17ChemAxon
pKa (Strongest Acidic)19.4ChemAxon
pKa (Strongest Basic)-0.87ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.46 m³·mol⁻¹ChemAxon
Polarizability19.07 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H18O
IUPAC name2-(4-methylcyclohex-3-en-1-yl)propan-2-ol
InChI IdentifierInChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3
InChI KeyWUOACPNHFRMFPN-UHFFFAOYSA-N
Isomeric SMILESCC1=CCC(CC1)C(C)(C)O
Average Molecular Weight154.253
Monoisotopic Molecular Weight154.1357652
Classification
Description Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Tertiary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 77.87%; H 11.76%; O 10.37%DFC
Melting Point37.5 oC
Boiling PointNot Available
Experimental Water Solubility0.71 mg/mL at 25 oCLI,J & PERDUE,EM (1995)
Experimental logP2.98LI,J & PERDUE,EM (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSalpha-Terpineol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9100000000-5e78cee1bf957533902eSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-1900000000-b06b43c06bcab8a8b2002016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052k-9600000000-ecd246742e68c77c01352016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-100r-9200000000-7b4cf8729bfcea55f85c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-cdc8abcd2a8d0f849b012016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-4900000000-28a4ee193904ac2aac652016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000b-9400000000-24758c06f5cf794027aa2016-08-03View Spectrum
NMRNot Available
ChemSpider ID390927
ChEMBL IDNot Available
KEGG Compound IDC09902
Pubchem Compound ID442501
Pubchem Substance IDNot Available
ChEBI ID22469
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04043
CRC / DFC (Dictionary of Food Compounds) IDJQJ06-Z:JQJ06-Z
EAFUS ID3608
Dr. Duke IDTERPINEOL|ALPHA-TERPINEOL
BIGG IDNot Available
KNApSAcK IDC00029674
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID98-55-5
GoodScent IDrw1011251
SuperScent IDNot Available
Wikipedia IDTerpineol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Angiotensin converting enzyme inhibitor35457 An agent that blocks the conversion of angiotensin I to angiotensin II, reducing blood pressure and fluid retention. Therapeutically, it's used to treat hypertension, heart failure, and protect kidney function in diabetes, thereby reducing the risk of cardiovascular disease and stroke.DUKE
Aldose reductase inhibitor48550 An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.DUKE
AllelopathicBiochemicals that inhibit growth, survival, or reproduction in other organisms, with potential therapeutic applications in weed control, antimicrobial, and anticancer treatments, and key medical uses in developing novel pesticides, antibiotics, and chemotherapeutics.DUKE
Analgesic35480 An agent that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.DUKE
AnestheticA drug that induces a reversible loss of sensation, used to prevent pain and discomfort during medical procedures, surgeries, and diagnostic tests, promoting patient comfort and facilitating treatment.DUKE
Anti-acne50177 An agent that reduces acne symptoms, commonly used in managing acne vulgaris by minimizing oil production, preventing clogged pores, and decreasing bacterial growth, thereby reducing inflammation and promoting healthy skin.DUKE
Anti-allergenic50857 An agent that reduces or blocks allergic reactions, commonly used to treat conditions such as hay fever, asthma, and skin allergies, by inhibiting the release of histamine and other inflammatory mediators, providing relief from symptoms like itching, sneezing, and congestion.DUKE
Anti-asthmatic49167 An agent that relieves bronchospasm and inflammation, commonly used to manage asthma symptoms, chronic obstructive pulmonary disease (COPD), and other respiratory disorders, improving lung function and overall respiratory health.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti-cancer35610 An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival.DUKE
Anti cariogenic52217 An agent that prevents tooth decay, reducing bacterial acid production and plaque formation. Its biological role is to inhibit the growth of cariogenic bacteria, and its therapeutic applications include preventing dental caries and managing tooth decay. Key medical uses include toothpaste, mouthwashes, and dental varnishes to maintain oral health.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti proliferantAn agent that prevents or inhibits cell growth and division, used therapeutically to treat cancer, manage tumor growth, and prevent restenosis after angioplasty, reducing abnormal cell proliferation.DUKE
Anti septic33281 An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.DUKE
Anti-spasmodic52217 An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.DUKE
Anti-tussive52217 An agent that suppresses coughing, reducing the frequency and severity of coughs. It works by targeting the brain's cough center, providing therapeutic relief for dry, irritating coughs. Key medical uses include managing coughs associated with colds, flu, and other respiratory conditions.DUKE
CholagogueAn agent that stimulates the release of bile from the gallbladder, promoting digestion and relieving bile duct issues. Therapeutically, it aids in treating gallstones, jaundice, and liver disorders, while also supporting digestive health.DUKE
CicatrizantAn agent that promotes wound healing by forming scar tissue, reducing inflammation and tissue damage. Therapeutically, it aids in tissue repair and regeneration, commonly used in treating skin conditions, wounds, and burns, to minimize scarring and promote recovery.DUKE
CulicideAn agent that destroys mosquitoes, playing a crucial role in preventing the spread of mosquito-borne diseases. Its therapeutic applications include vector control, and key medical uses include preventing malaria, dengue fever, and Zika virus transmission.DUKE
Expectorant52217 An agent that thins and loosens mucus, making it easier to cough up, reducing congestion. It aids in clearing respiratory tract secretions, commonly used to relieve coughs, colds, and bronchitis, promoting easier breathing and soothing irritated airways.DUKE
Name48318 flavorDUKE
Insecticide24852 An agent that kills or repels insects, used to control pests and prevent disease transmission. Therapeutically, insecticides have applications in public health and veterinary medicine, key medical uses include controlling insect-borne diseases such as malaria, typhus, and Lyme disease.DUKE
Insectifuge24852 A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission.DUKE
Interleukin-6 inhibitor35222 An agent that blocks the activity of interleukin-6, a cytokine involved in inflammation and immune response. Therapeutically, it reduces inflammation and is used to treat autoimmune diseases, such as rheumatoid arthritis, and certain types of cancer.DUKE
LarvicideAn insecticide that targets the larval life stage of insects, preventing their development into adults. Its biological role is to control insect populations, and its therapeutic applications include managing mosquito-borne diseases such as malaria and dengue fever, as well as controlling pest infestations in agriculture and public health.DUKE
Mosquitofuge24852 A natural compound that repels mosquitoes, playing a biological role in plant defense. It has therapeutic applications in preventing insect-borne diseases and key medical uses in developing insect repellents and protective measures against mosquito-borne illnesses such as malaria and dengue fever.DUKE
Motor depressantAn agent that reduces the normal functioning level of motor neurons, mainly in voluntary muscles, used to treat conditions such as muscle spasms, seizures, and anxiety disorders, promoting relaxation and relieving symptoms.DUKE
Nematicide25491 An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health.DUKE
Perfumery48318 The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Sedative35717 An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.DUKE
TermiticideAn agent that kills termites, used to control termite infestations and prevent damage to structures and wood.DUKE
TransdermalA route of administration where active ingredients are delivered through the skin for systemic distribution, used therapeutically to manage conditions like pain, hormone replacement, and smoking cessation, with key medical applications including patches and implants for controlled release of medications.DUKE
Vulnerary73336 An agent that promotes wound healing, tissue repair, and skin regeneration. It facilitates the biological process of recovery, reducing inflammation and infection. Therapeutically, vulneraries are used to treat cuts, burns, ulcers, and other skin injuries, supporting the body's natural healing mechanisms and minimizing scarring.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
oil
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
anise
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
mint
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
pine
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
terpene
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
lilac
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
citrus
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.