AFCDB: 7-Methyl-3-methylene-1,6-octadiene (FDB017400)

Record Information

Version

1.0

Creation date

2010-04-08 22:13:04 UTC

Update date

2020-09-17 15:34:51 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

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

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Property	Value	Reference
Boiling Point	Bp8.5 51-51.5°	DFC
Charge	Not Available
Density	Not Available
Experimental logP	4.17	CHEMICALS INSPECTION AND TESTING INSTITU (
Experimental pKa	Not Available
Experimental Water Solubility	0.0056 mg/mL at 25 oC	CHEMICALS INSPECTION AND TESTING INSTITU (1992)
Isoelectric point	Not Available
Mass Composition	C 88.16%; H 11.84%	DFC
Melting Point	<-10 oC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

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

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Carrot	13.000 - 13.000 mg/100 g	13.000 mg/100 g	DUKE, 12926889, David M. Alabran, Howard R. Moskowitz, and Ahmed F. Mabrouk. Carrot-Root Oil Components and Their Dimensional Characterization of Aroma. J. Agr. Food Chem. 1975, 23(2), 229-232. DOI: 10.1021/jf60198a031, Robert G Schaller, Wilfried H Schnitzler. Nitrogen nutrition and flavour compounds of carrots (Daucus carota L) cultivated in Mitscherlich pots. J Sci Food Agric 80:49-56 (2000), Ron G. Buttery, Richard M. Seifert, Dante G. Guadagni, Dale R. Black, and Louisa. Ling. Characterization of some volatile constituents of carrots. J. Agric. Food Chem., 1968, 16 (6), pp 1009-1015 DOI: 10.1021/jf60160a012, Varming, C., Jensen, K., Moller, S., Brockhoff, P. B., Christiansen, T., Edelenbos, M., et al. (2004). Eating quality of raw carrots -- correlations between flavour compounds, sensory profiling analysis and consumer liking test. Food Quality and Preference, 15, 531-540, PATHBANK
Dill	50.400 - 50.400	50.400	DUKE, PATHBANK
Green bell pepper	Expected but not quantified	Not Available	DUKE, PATHBANK
Oat	Expected but not quantified	Not Available	DUKE, PATHBANK
Orange bell pepper	Expected but not quantified	Not Available	DUKE, PATHBANK
Parsnip	Expected but not quantified	Not Available	DUKE, PATHBANK
Red bell pepper	Expected but not quantified	Not Available	DUKE, PATHBANK
Yellow bell pepper	Expected but not quantified	Not Available	DUKE, PATHBANK
Barley	Expected but not quantified	Not Available	PATHBANK
Broccoli	Expected but not quantified	Not Available	PATHBANK

Showing 1 to 10 of 37 entries

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
aldose reductase inhibitor	48550	An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).	DUKE
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
analgesic	35480	An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.	DUKE
angiotensin converting enzyme inhibitor	35457	An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti convulsant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti mutagenic			DUKE
anti nitrosaminic			DUKE
anti nociceptive	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE

Showing 1 to 10 of 22 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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

Showing 1 to 8 of 8 entries

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not 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.

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

Structure for FDB017400 (7-Methyl-3-methylene-1,6-octadiene)