Showing Compound 7-Methyl-3-methylene-1,6-octadiene (FDB017400)

Record Information

Version

1.0

Creation date

2010-04-08 22:13:04 UTC

Update date

2025-11-19 01:54:03 UTC

Primary ID

FDB017400

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

7-Methyl-3-methylene-1,6-octadiene

Description

Œ≤-Myrcene or myrcene is an acyclic monoterpene. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Œ≤-Myrcene is a significant component of the essential oil of several plants, including allspice, bay, hops, houttuynia, lemon grass, mango, myrcia, verbena, west indian bay tree, and cardamom. It is also the main component of wild thyme, the leaves of which contain up to 40% by weight of myrcene. Industrially, it is produced mainly semi-synthetically from myrcia, from which it gets its name. Œ≤-Myrcene is a flavouring agent and it is used in the perfumery industry. It has a pleasant odor but is rarely used directly. It is a key intermediate in the production of several fragrances such as menthol, citral, citronellol, citronellal, geraniol, nerol, and linalool.

CAS Number

123-35-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
7-Methyl-3-methylene-1,6-octadiene	ChEBI
7-Methyl-3-methyleneocta-1,6-diene	ChEBI
Myrcene	ChEBI
b-Myrcene	Generator
Β-myrcene	Generator
2-Methyl-6-methylene-1,7-octadiene	MeSH
2-Methyl-6-methylene-2,7-octadiene	HMDB
3-Methylene-7-methyl-1, 6-octadiene	HMDB
3-Methylene-7-methyl-1,6-octadiene	HMDB
7-Methyl-3-methylene-1,6-octadiene (beta -myrcene)	HMDB
7-Methyl-3-methylene-1,6-octadiene (myrcene)	HMDB
7-Methyl-3-methylene-octa-1,6-diene	HMDB
7-Methyl-3-methyleneoctadiene-(1,6)	HMDB
7-Methyl-3-methylideneocta-1,6-diene	HMDB
b-Geraniolene	HMDB
beta-Mircene	HMDB
beta-Myrcene	HMDB, KEGG
FEMA 2762	HMDB
beta-Geraniolene	HMDB
β-Geraniolene	HMDB
β-mircene	biospider
β-myrcene	biospider
1, 6-Octadiene, 7-methyl-3-methylene-	biospider
1,6-Octadiene, 7-methyl-3-methylene-	biospider
7-methyl-3-methylene-1,6-octadiene (β-myrcene)	biospider
7-methyl-3-methylene-1,6-octadiene (myrcene)	biospider
7-methyl-3-methyleneocta-1,6-diene	biospider
7-methyl-3-methylideneocta-1,6-diene	biospider
B-geraniolene	biospider
beta -Mircene	HMDB
beta -Myrcene	HMDB
Beta-myrcene	biospider
β-myrcene	Generator

Predicted Properties

Property	Value	Source
Water Solubility	0.078 g/L	ALOGPS
logP	4.32	ALOGPS
logP	3.54	ChemAxon
logS	-3.2	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	48.38 m³·mol⁻¹	ChemAxon
Polarizability	17.53 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H16

IUPAC name

7-methyl-3-methylideneocta-1,6-diene

InChI Identifier

InChI=1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7H,1,4,6,8H2,2-3H3

InChI Key

UAHWPYUMFXYFJY-UHFFFAOYSA-N

Isomeric SMILES

CC(C)=CCCC(=C)C=C

Average Molecular Weight

136.238

Monoisotopic Molecular Weight

136.125200515

Classification

Description

Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Acyclic monoterpenoids

Alternative Parents

Substituents

Acyclic monoterpenoid
Branched unsaturated hydrocarbon
Alkatriene
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Acyclic olefin
Hydrocarbon
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

monoterpene (CHEBI:17221 )
Acyclic monoterpenoids (C06074 )
Linear monoterpenes (C06074 )
Acyclic monoterpenoids (LMPR0102010005 )
a monoterpenoid (CPD-4888 )

Ontology

Ingestion

Source:

Biological:

Animal

Plant:

Poaceae

Biological location:

Cell and elements:

Extracellular

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 88.16%; H 11.84%	DFC
Melting Point	<-10 oC
Boiling Point	Bp8.5 51-51.5°	DFC
Experimental Water Solubility	0.0056 mg/mL at 25 oC	CHEMICALS INSPECTION AND TESTING INSTITU (1992)
Experimental logP	4.17	CHEMICALS INSPECTION AND TESTING INSTITU (
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	[neutral] lmax 226 (e 16100) (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-0044238938af2a674670	2014-09-20	View Spectrum
GC-MS	7-Methyl-3-methylene-1,6-octadiene, non-derivatized, GC-MS Spectrum	splash10-00kf-9000000000-94249d5850d02862868d	Spectrum
GC-MS	7-Methyl-3-methylene-1,6-octadiene, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-078927c5db5ba8691e12	Spectrum
GC-MS	7-Methyl-3-methylene-1,6-octadiene, non-derivatized, GC-MS Spectrum	splash10-00kf-9000000000-94249d5850d02862868d	Spectrum
GC-MS	7-Methyl-3-methylene-1,6-octadiene, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-078927c5db5ba8691e12	Spectrum
GC-MS	7-Methyl-3-methylene-1,6-octadiene, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-4934a34348f1966a1b57	Spectrum
Predicted GC-MS	7-Methyl-3-methylene-1,6-octadiene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0gbc-9100000000-3140926424077f6fe821	Spectrum
Predicted GC-MS	7-Methyl-3-methylene-1,6-octadiene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	7-Methyl-3-methylene-1,6-octadiene, 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	splash10-000i-3900000000-3c559009ab39d35fd493	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0019-9600000000-a02add9ea09761212874	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-c2cf7f8831e68542008b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-6882dc5ecf3f017e6584	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-c44cd1555bbebb14f177	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9700000000-b1c0f8495736a8fba510	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9000000000-ff2818480f196b4f5802	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05q9-9000000000-62442276cecbb1e6975b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0v00-9000000000-671d242601a78647a09d	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-7b99763f2098a29c1bd6	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-9815af0088c9d73412b6	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-24167ae6962b4d56019f	2021-09-24	View Spectrum

NMR

Type	Description		View
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, CDCl₃, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17221

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB38169

CRC / DFC (Dictionary of Food Compounds) ID

KXM92-T:KXM92-T

EAFUS ID

2622

Dr. Duke ID

MYRCENE|BETA-MYRCENE

BIGG ID

Not Available

KNApSAcK ID

C00000853

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

123-35-3

GoodScent ID

rw1016531

SuperScent ID

Not Available

Wikipedia ID

Myrcene

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
Angiotensin converting enzyme inhibitor	35457	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 inhibitor	48550	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
Allergenic	50904	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
Analgesic	35480	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
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-mutagenic		An agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.	DUKE
Anti-nitrosaminic		An agent that inhibits the formation of nitrosamines, carcinogenic compounds. It plays a biological role in cancer prevention, with therapeutic applications in reducing the risk of tobacco-related and other cancers. Key medical uses include chemoprevention and protection against carcinogenic exposures.	DUKE
Anti nociceptive	35470	An agent that reduces the sensitivity to painful stimuli, blocking the transmission of pain signals. Its biological role is to modulate pain perception, with therapeutic applications in managing acute and chronic pain. Key medical uses include treating headaches, arthritis, and post-surgical pain, as well as providing relief for cancer and neuropathic pain.	DUKE
Anti-oxidant	22586	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-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
Cancer preventive	35610	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
Chemopreventive	35610	An agent that prevents or delays the development of cancer, reducing the risk of tumor formation and progression. It plays a biological role in inhibiting carcinogenesis, and has therapeutic applications in cancer prevention, with key medical uses including reducing the risk of colorectal, breast, and prostate cancers.	DUKE
Name	48318	flavor	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
Hypothermic		A condition of abnormally low body temperature, playing a biological role in reducing metabolic rate and oxygen demand. Therapeutically, it has applications in neuroprotection, cardiac surgery, and trauma care. Key medical uses include treating heatstroke, cardiac arrest, and brain injuries, as well as preserving organs for transplantation.	DUKE
Insectifuge	24852	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
Irritant		An 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
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
Cytochrome-P450-2B1 inhibitor	50183	An agent that blocks the activity of cytochrome-P450-2B1, an enzyme involved in drug metabolism. Therapeutically, it reduces toxicity and enhances efficacy of certain medications, commonly used in managing cancer, neurological disorders, and drug interactions.	DUKE
Perfumery	48318	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
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

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
balsamic	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
must	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
spice	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
peppery	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
terpene	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
balsam	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
plastic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.