Record Information
Version1.0
Creation date2010-04-08 22:05:31 UTC
Update date2020-09-17 15:36:19 UTC
Primary IDFDB002793
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAnethole
DescriptionAnethole or 1-Methoxy-4(1-propenyl)-benzene, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Anethole is an extremely weak basic (essentially neutral) compound (based on its pKa). Anethol is a naturally occurring organic compound found in the essential oils of many plants such as anise, fennel, anise myrtle, liquorice as their large component of the odor and flavor. Anethole is a sweet, anise, and balsam tasting compound. It is used as a flavoring agent in alcoholic drinks and in small quantities in natural berry flavors. Anethole is found in a lower concentration in peppermints, wild celeries, and corianders. Anethole has also been detected, but not quantified in, several different foods, such as nutmegs, cumins, lemon balms, common thymes, and herbs and spices. This could make anethole a potential biomarker for the consumption of these foods. Anethole has potent antimicrobial, nematicidal and antifungal activities (PMID:11807977, 17078111, 18944489). There are two known anethol isomers including Cis- and Trans-anethol.
CAS Number4180-23-8
Structure
Thumb
Synonyms
SynonymSource
1-Methoxy-4-[(1Z)-prop-1-en-1-yl]benzeneChEBI
(e)-1-(4-Methoxyphenyl)propeneHMDB
(e)-1-Methoxy-4-(1-propenyl)benzeneHMDB
(e)-1-P-MethoxyphenylpropeneHMDB
(e)-AnetholHMDB
(e)-AnetholeHMDB
(e)-P-PropenylanisoleHMDB
1-(4-Methoxyphenyl)-1(3)-propeneHMDB
1-(Methyloxy)-4-[(1E)-prop-1-en-1-yl]benzeneHMDB
1-(P-Methoxyphenyl)-propeneHMDB
1-Methoxy-4-((1E)-1-propenyl)benzeneHMDB
1-Methoxy-4-(1-propenyl)-(e)-benzeneHMDB
1-Methoxy-4-(1-propenyl)benzene, 9ciHMDB
1-Methoxy-4-(1E)-1-propen-1-yl-benzeneHMDB
1-Methoxy-4-(1E)-1-propenyl-benzeneHMDB
1-Methoxy-4-(propen-1-yl)-benzeneHMDB
1-Methoxy-4-(propenyl)-benzeneHMDB
1-Methoxy-4-propenylbenzeneHMDB
1-Methoxy-4-[(1E)-prop-1-en-1-yl]benzeneHMDB
4-Methoxy-1-propenylbenzeneHMDB
4-MethoxypropenylbenzeneHMDB
4-PropenylanisoleHMDB
Anethole, usanHMDB
Anise camphorHMDB
Anisole, P-propenyl-, (e)- (8ci)HMDB
AnistearopteneHMDB
e-AnetholeHMDB
FEMA 2086HMDB
IsoestragoleHMDB
Methoxy-4-propenylbenzeneHMDB
P-AnetholeHMDB
P-Propenyl-trans-anisoleHMDB
P-Propenylanisole, 8ciHMDB
P-Propenylphenyl methyl etherHMDB
trans-1-(4-Methoxyphenyl)-1-propeneHMDB
trans-1-(P-Methoxyphenyl)-1-propeneHMDB
trans-1-(P-Methoxyphenyl)propeneHMDB
trans-1-Methoxy-4-(1-propenyl)benzeneHMDB
trans-1-P-AnisylpropeneHMDB
trans-4-(1-Propenyl)anisoleHMDB
trans-AnetholeHMDB
trans-Anise camphorHMDB
trans-P-AnetholeHMDB
trans-P-Methoxy-beta-methylstyreneHMDB
trans-P-PropenylanisoleHMDB
(E)-1-(4-Methoxyphenyl)propenebiospider
(E)-1-Methoxy-4-(1-propenyl)benzenebiospider
(E)-1-p-Methoxyphenylpropenebiospider
(E)-Anetholbiospider
(E)-anetholebiospider
(E)-p-propenylanisolebiospider
1-Methoxy-4-(1-propenyl)benzene, (E)-biospider
1-Methoxy-4-(1-propenyl)benzene, 9CIdb_source
1-methoxy-4-[(1E)-prop-1-en-1-yl]benzenebiospider
Anethole, USANdb_source
Anisole, p-propenyl-, (E)- (8CI)biospider
Anisole, p-propenyl-, trans-biospider
Benzene, 1-methoxy-4-(1-propenyl)-, (E)-biospider
Benzene, 1-methoxy-4-(1E)-1-propen-1-yl-biospider
Benzene, 1-methoxy-4-(1E)-1-propenyl-biospider
Benzene, 1-methoxy-4-(propen-1-yl)-biospider
Benzene, 1-methoxy-4-(propenyl)-biospider
E-anetholebiospider
Methoxy-beta-methylstyrene, trans-p-biospider
P-anetholebiospider
p-Propenylanisole, 8CIdb_source
P-propenylphenyl methyl etherbiospider
Propene, 1-(p-methoxyphenyl)-biospider
trans-1-(p-Methoxyphenyl)-1-propenebiospider
trans-1-(p-Methoxyphenyl)propenebiospider
trans-1-p-Anisylpropenebiospider
Trans-anetholebiospider
Trans-anise camphorbiospider
Trans-p-anetholebiospider
Trans-p-methoxy-beta-methylstyrenebiospider
Trans-p-propenylanisolebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP3.4ALOGPS
logP2.94ChemAxon
logS-2.9ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.88 m³·mol⁻¹ChemAxon
Polarizability17.21 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H12O
IUPAC name1-methoxy-4-[(1Z)-prop-1-en-1-yl]benzene
InChI IdentifierInChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3-
InChI KeyRUVINXPYWBROJD-ARJAWSKDSA-N
Isomeric SMILESCOC1=CC=C(\C=C/C)C=C1
Average Molecular Weight148.2017
Monoisotopic Molecular Weight148.088815006
Classification
Description Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassAnisoles
Direct ParentAnisoles
Alternative Parents
Substituents
  • Phenoxy compound
  • Methoxybenzene
  • Styrene
  • Anisole
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateliquid
Physical DescriptionNot Available
Mass CompositionC 81.04%; H 8.16%; O 10.80%DFC
Melting PointMp 22.5°DFC
Boiling PointBp 235°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data[neutral] lmax 259 (e 22300) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAnethole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000t-2900000000-0665985a70ac9c27eb53Spectrum
Predicted GC-MSAnethole, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-436711faeb648ff2a2d52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-2900000000-7d9dfbe23492f9be6a292016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fr6-9600000000-582716ef7e52a802bbc12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-e66c5cd440af8e6d0c882016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-709cb24546c67c386dde2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-3900000000-ecda3d7970e587876f662016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-c2f74e33d816bec66aa02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-5aa2093882ee9ccdc8862021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3900000000-03b30da0f9adb9d580ff2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-d856cd34f2f6f83def662021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-2900000000-b32a050861e7a927efa52021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9100000000-e059cbeab65dc16bd3b42021-09-23View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID637563
Pubchem Substance IDNot Available
ChEBI ID35616
Phenol-Explorer ID645
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHBT07-B:CNR12-S
EAFUS ID213
Dr. Duke IDANETHOL|ANETHOLE|TRANS-ANETHOLE
BIGG IDNot Available
KNApSAcK IDC00029334
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1001151
SuperScent ID637563
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Allergenic50904 A substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.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 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 genotoxic52217 An agent that prevents or reduces genetic damage, protecting cells from harmful mutations. It plays a biological role in maintaining genome stability and has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing chemotherapy side effects and protecting against environmental toxins.DUKE
Anti hepatotic62868 An agent that protects the liver from damage, reducing inflammation and promoting liver health. It is used therapeutically to manage liver diseases, such as hepatitis and cirrhosis, and to prevent liver damage from toxins and medications. Key medical uses include treating liver conditions, supporting liver function, and preventing liver failure.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 NF-kappa-B35222 An agent that inhibits the activity of NF-kappa-B, a protein complex involved in inflammation and immune responses. It reduces inflammation and has therapeutic applications in managing autoimmune diseases, cancer, and inflammatory disorders, with key medical uses including treatment of rheumatoid arthritis, asthma, and certain types of cancer.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti radicularAn agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.DUKE
Anti-salmonella33282 An agent that targets and eliminates Salmonella bacteria, reducing the risk of food poisoning and gastrointestinal infections. Therapeutically, it is used to treat salmonellosis, a disease caused by Salmonella infection, and to prevent outbreaks in high-risk individuals, such as those with weakened immune systems.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 TNF35222 An agent that blocks tumor necrosis factor, a pro-inflammatory cytokine, reducing inflammation and immune responses. Therapeutically used to treat autoimmune diseases, such as rheumatoid arthritis, psoriasis, and Crohn's disease, by mitigating inflammation and tissue damage.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Anti-yeast33281 An agent that inhibits the growth of yeast, playing a role in preventing fungal infections. Therapeutically, it is used to treat conditions such as candidiasis and athlete's foot, and has applications in managing digestive issues and skin infections.DUKE
Calcium antagonist48706 A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
CandidicideAn agent that kills Candida species, such as Candida albicans, reducing fungal infections. Therapeutically, it is used to treat candidiasis, with key medical applications in managing oral thrush, vaginal yeast infections, and other fungal diseases.DUKE
CarminativeAn agent that prevents or relieves gas in the gastrointestinal tract, facilitating its expulsion and combating flatulence, commonly used to soothe digestive issues and alleviate symptoms of bloating and discomfort.DUKE
DermatitigenicAn agent that causes inflammation of the skin (dermatitis), triggering allergic reactions and immune responses. Its biological role involves activating immune cells, leading to skin irritation. Therapeutically, it is used to test skin sensitivity and develop treatments for dermatitis. Key medical uses include diagnosing skin allergies and researching dermatitis treatments.DUKE
DigestiveAn agent that aids with digestion, breaking down food into absorbable components. It plays a biological role in nutrient absorption, has therapeutic applications in managing digestive disorders, and key medical uses include treating indigestion, bloating, and malabsorption.DUKE
EstrogenicAn agent that mimics the effects of estrogen, regulating female reproductive processes and development. Therapeutically, estrogenic agents are used in hormone replacement therapy, contraception, and treating menopausal symptoms, as well as certain cases of osteoporosis and infertility.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
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
Gastrostimulant55324 An agent that stimulates digestive motility, increasing gastrointestinal movement and secretion. It enhances gut function, relieving symptoms of gastroparesis, constipation, and other motility disorders, commonly used in managing conditions like diabetes-related gastroparesis and postoperative ileus.DUKE
Hepatotoxic50908 An agent that causes liver damage or toxicity, disrupting normal liver function. It has no therapeutic applications, but is often a side effect of certain medications, such as acetaminophen overdose, and is a key consideration in medical uses, including monitoring liver function during drug therapy.DUKE
Immunostimulant50847 An agent that stimulates the immune system, enhancing its response to infections and diseases. Therapeutically, it boosts the body's natural defenses, commonly used to treat immunodeficiency disorders, prevent infections, and support cancer treatment, as well as manage chronic conditions like hepatitis and HIV.DUKE
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
IrritantAn agent that causes slight inflammation or discomfort, stimulating a biological response. Therapeutically, it can be used to increase blood flow or stimulate healing. Key medical uses include treating wounds, skin conditions, and respiratory issues, such as congestion, by inducing a mild inflammatory response to promote recovery.DUKE
LactagogueAn agent that stimulates milk production, aiding breastfeeding. It promotes lactation, commonly used to treat low milk supply, and supports maternal health in postpartum care.DUKE
LeucocytogenicAn agent that stimulates the formation of leucocytes (white blood cells), playing a biological role in immune system regulation. Therapeutically, it is used to treat conditions associated with low white blood cell count, such as leukemia and infections, and to support recovery after chemotherapy or bone marrow transplantation.DUKE
MutagenicAn agent that induces genetic mutations, altering DNA sequences. It plays a biological role in evolution and adaptation. Therapeutically, mutagenic agents are used in cancer treatment, such as chemotherapy, and in gene therapy to introduce beneficial traits. Key medical uses include oncology and genetic research.DUKE
Nephroprotective76595 An agent that protects the kidneys from damage, reducing inflammation and oxidative stress. Therapeutically, it helps prevent or treat kidney diseases, such as nephropathy and acute kidney injury, and is used in managing conditions like diabetes and hypertension to preserve renal function.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
SecretogogueA substance that stimulates secretion, playing a biological role in regulating hormone and enzyme release. Therapeutically, it has applications in treating conditions like hyposecretion and is used to manage digestive issues, respiratory problems, and endocrine disorders, promoting healthy secretion in various bodily systems.DUKE
SecretolyticAn agent that increases serous mucus production in the respiratory tract, aiding in clearing debris and excess mucus. Its therapeutic applications include relieving respiratory congestion and coughs, making it useful in managing conditions like bronchitis, asthma, and chronic obstructive pulmonary disease (COPD).DUKE
Sweetener50505 A substance that adds sweetness to food and beverages, often used as a sugar substitute. Its biological role is to stimulate taste receptors, while its therapeutic applications include managing calorie intake and blood sugar levels. Key medical uses include treating diabetes and obesity, as well as reducing tooth decay risk.DUKE
Sympathomimetic35524 An agent that mimics the effects of the sympathetic nervous system, increasing heart rate, blood pressure, and energy. Therapeutically, it's used to treat conditions like asthma, hypotension, and shock, as well as nasal decongestion and eye dilation.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
anise
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
balsam
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
licorice
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
mimosa
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
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).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.