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M100005

Sigma-Aldrich

Myrcene

technical grade

Synonym(s):

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

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About This Item

Linear Formula:
H2C=CHC(=CH2)CH2CH2CH=C(CH3)2
CAS Number:
123-35-3
Molecular Weight:
136.23
Beilstein:
1719990
EC Number:
204-622-5
MDL number:
MFCD00008908
UNSPSC Code:
12352100
PubChem Substance ID:
24896464
NACRES:
NA.22

grade

technical grade

Quality Level

200

vapor density

4.7 (vs air)

vapor pressure

~7 mmHg ( 20 °C)

contains

0.1% alpha-tocopherol

refractive index

n20/D 1.469 (lit.)

bp

167 °C (lit.)

solubility

water: soluble 0.00109 g/L at 20 °C

density

0.791 g/mL at 25 °C (lit.)

storage temp.

−20°C

SMILES string

C\C(C)=C/CCC(=C)C=C

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

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General description

Myrcene is a monoterpene. Males of Ips spp. produced the pheromones ipsdienol (2-methyl-6-methylene-2,7-octadien-4-ol) and/or ipsenol (2-methyl-6-methylene-7-octen-4-ol) on exposure to the vapours of myrcene. Myrcene serves as a precursor for terpene alcohols. Myrcene is a constituent of the beetle′s host, ponderosapine. Hydrogenation of myrcene catalyzed by Ru, Cr, Ir and Rh complexes yields a complex mixture of mono-, di- and trihydrogenated products.

Application

Myrcene is the suitable synthetic standard used in the identification of E-myrcenol (2-methyl-6-methylene-E-2,7-octadien-1-01) as a major hindgut constituent in Eurasian bark beetle Ips duplicatus by GC-MS.

Signal Word

Danger

Hazard Statements

H226,H304,H315,H319,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Asp. Tox. 1 - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

111.2 °F - closed cup

Flash Point(C)

44 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Selective hydrogenation of myrcene catalyzed by complexes of ruthenium, chromium, iridium and rhodium.
Speziali MG, et al.
J. Mol. Catal. A: Chem., 239(1), 10-14 (2005)
W D Bedard et al.
Science (New York, N.Y.), 164(3885), 1284-1285 (1969-06-13)
In the field, both sexes of the western pine beetle, Dendroctonus brevicomis, are attracted by the female-produced bicyclic ketal exo-brevicomin; this response is enhanced by myrcene (a constituent of the beetle's host, ponderosapine), which is not an attractant by itself.
E-myrcenol inIps duplicatus: An aggregation pheromone component new for bark beetles.
Byers JA, et al.
Experientia, 46(11-12), 1209-1211 (1990)
Myrcene: a precursor of pheromones in Ips beetles.
P R Hughes
Journal of insect physiology, 20(7), 1274-1275 (1974-07-01)
Mark L Thompson et al.
Applied microbiology and biotechnology, 85(3), 721-730 (2009-08-27)
The biocatalytic generation of high-value chemicals from abundant, cheap and renewable feedstocks is an area of great contemporary interest. A strain of Rhodococcus erythropolis designated MLT1 was isolated by selective enrichment from the soil surrounding hop plants, using the abundant
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