Showing Compound trans-Isoasarone (FDB008006)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:52 UTC

Update date

2020-02-24 19:10:48 UTC

Primary ID

FDB008006

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

trans-Isoasarone

Description

trans-Isoasarone, also known as asarone or cis-isoelemicin, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. trans-Isoasarone is found, on average, in the highest concentration within wild carrots (Daucus carota) and carrots (Daucus carota ssp. sativus). This could make trans-isoasarone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on trans-Isoasarone.

CAS Number

2883-98-9

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Asarone	ChEBI
trans-1,2,4-Trimethoxy-5-(1-propenyl)benzene	ChEBI
trans-Isoasaron	ChEBI
Asarone, (e)-isomer	MeSH
Asarone, (Z)-isomer	MeSH
cis-Isoelemicin	MeSH
gamma-Asarone	MeSH
(e)-Asarone	MeSH
(Z)-Asarone	MeSH
Isoasarone	MeSH
2,4,5-Trimethoxypropen-1-ylbenzene	MeSH
beta-Asarone	MeSH
cis-beta-Asarone	MeSH
cis-Isoasarone	MeSH
trans-Asarone	MeSH
trans-Isoasarone	ChEBI
a-Asaron	Generator, HMDB
α-asaron	Generator, HMDB
(e)-2,4,5-Trimethoxypropenylbenzene	HMDB
1,2,4-Trimethoxy-5-(1-propenyl)-(e)-benzene	HMDB
1,2,4-Trimethoxy-5-propenyl-(e)-benzene	HMDB
1,2,4-Trimethoxy-5-propenyl-trans-benzene	HMDB
1,2,4-Trimethoxy-5-[(1E)-1-propenyl]benzene	HMDB
alpha-Asarone	HMDB
Isoasaron (6ci)	HMDB
trans-(alpha )-Asarone	HMDB
trans-2,4,5-Trimethoxypropenylbenzene	HMDB
a-Asarone	Generator
Α-asarone	Generator
(E)-2,4,5-Trimethoxypropenylbenzene	biospider
(E)-Asarone	biospider
Benzene, 1,2,4-trimethoxy-5-(1-propenyl)-, (E)-	biospider
Benzene, 1,2,4-trimethoxy-5-propenyl-, (E)-	biospider
Benzene, 1,2,4-trimethoxy-5-propenyl-, trans-	biospider
Isoasaron (6CI)	manual
Trans-(α)-asarone	biospider
Trans-asarone	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.35 g/L	ALOGPS
logP	3.35	ALOGPS
logP	2.62	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	27.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	60.81 m³·mol⁻¹	ChemAxon
Polarizability	23.24 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C12H16O3

IUPAC name

1,2,4-trimethoxy-5-[(1E)-prop-1-en-1-yl]benzene

InChI Identifier

InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5+

InChI Key

RKFAZBXYICVSKP-AATRIKPKSA-N

Isomeric SMILES

COC1=CC(OC)=C(\C=C\C)C=C1OC

Average Molecular Weight

208.2536

Monoisotopic Molecular Weight

208.109944378

Classification

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

asarone (CHEBI:78309 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Plant

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	62-63 oC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	trans-Isoasarone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00mo-1910000000-311a6eeb6d6e7b8cbd71	Spectrum
Predicted GC-MS	trans-Isoasarone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	trans-Isoasarone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0190000000-43c2db0c78cd2c38866d	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-3890000000-8a310f43dfa83a6852fa	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gvo-5900000000-d8dec13738907307ac30	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-3260fe63f5df8a57e501	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4m-0930000000-d48f45f13f4ba95211b5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bt9-3900000000-ee6124b2b2fd1c4c5dc2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-48e778bb33693fbfbece	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0390000000-20df49cd5d736b546ff7	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9500000000-cb4f4e739e22509440dd	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-65fdf834be31e8e78310	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0980000000-1b5b7322afb6d52db845	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-8900000000-4428ce94cd47e6a5c986	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB31469

CRC / DFC (Dictionary of Food Compounds) ID

CNS74-R:CNS75-S

EAFUS ID

Not Available

Dr. Duke ID

ASARONE|TRANS-ISOASARONE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Anti bacterial	33282	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 convulsant	52217	An agent that reduces or prevents seizures, commonly used in managing epilepsy, neuropathic pain, and mood disorders, by stabilizing abnormal electrical activity in the brain.	DUKE
Anti-epileptic		An agent that reduces seizure activity, commonly used in managing epilepsy, neuropathic pain, and mood disorders, by stabilizing neuronal membranes and modulating neurotransmitter release.	DUKE
Anti pyretic	35493	An agent that reduces fever, commonly used to relieve headache, pain, and discomfort associated with elevated body temperature, and to manage fever in various medical conditions, such as infections and inflammatory diseases.	DUKE
Anti-spasmodic	52217	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
Bronchospasmolytic	52217	An agent that relaxes airway smooth muscle, preventing bronchospasm. It plays a biological role in regulating airway tone and is therapeutically used to treat respiratory conditions such as asthma and chronic obstructive pulmonary disease (COPD), providing relief from wheezing, coughing, and shortness of breath.	DUKE
Cardiodepressant	38070	An agent that slows heart rate and reduces cardiac contractility, used to manage conditions like hypertension, angina, and arrhythmias, reducing the heart's workload and oxygen demand.	DUKE
Central nervous system depressant	35470	An agent that slows brain activity, reducing anxiety, stress, and excitability. Therapeutically, it's used to manage insomnia, seizures, and anxiety disorders, promoting relaxation and sedation. Key medical uses include treating insomnia, epilepsy, and panic disorders, as well as inducing anesthesia.	DUKE
Emetic		An agent that induces vomiting, playing a biological role in expelling toxins from the body. Therapeutically, it is used to treat poisoning, overdose, or gastrointestinal obstruction. Key medical uses include managing drug toxicity and aiding in stomach pumping procedures.	DUKE
Fungicide	24127	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
Hypothalamic depressant		An agent that reduces hypothalamus activity, regulating pituitary gland function. It has therapeutic applications in managing conditions like hyperpituitarism, and key medical uses include treating hormonal imbalances, certain endocrine disorders, and regulating body temperature and appetite.	DUKE
Mutagenic		An 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
Myorelaxant		An agent that reduces muscle contractility by blocking nerve impulses or decreasing motor end plate excitability, used therapeutically to relieve muscle spasms, tension, and pain, commonly in managing musculoskeletal disorders, anxiety, and insomnia.	DUKE
Pesticide	25944	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
Psychoactive	35471	A substance that affects brain function, altering mood, perception, or consciousness. It plays a biological role in modifying neurotransmitter activity. Therapeutically, psychoactive substances have applications in managing mental health disorders, such as depression and anxiety. Key medical uses include treating psychiatric conditions, including attention deficit hyperactivity disorder (ADHD), and certain sleep disorders.	DUKE
Secretolytic		An 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
Sedative	35717	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
Tranquilizer		An agent that induces relaxation and reduces anxiety, used therapeutically to manage anxiety disorders, insomnia, and restlessness, promoting calmness and sedation in individuals.	DUKE