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M100005

Sigma-Aldrich

Myrcene

technical grade

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Synonym(s):
β-Myrcene, 7-Methyl-3-methylene-1,6-octadiene
Linear Formula:
H2C=CHC(=CH2)CH2CH2CH=C(CH3)2
CAS Number:
Molecular Weight:
136.23
Beilstein/REAXYS Number:
1719990
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

grade

technical grade

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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1 of 4

This Item
W276200W276212442475
vibrant-m

M100005

Myrcene

vibrant-m

W276200

Myrcene

vibrant-m

W276212

Myrcene

vibrant-m

442475

Benzo[e]pyrene

solubility

water: soluble 0.00109 g/L at 20 °C

solubility

-

solubility

-

solubility

-

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-30°C

refractive index

n20/D 1.469 (lit.)

refractive index

n20/D 1.469 (lit.)

refractive index

n20/D 1.469 (lit.)

refractive index

-

density

0.791 g/mL at 25 °C (lit.)

density

0.791 g/mL at 25 °C (lit.)

density

0.791 g/mL at 25 °C (lit.)

density

-

bp

167 °C (lit.)

bp

167 °C (lit.)

bp

167 °C (lit.)

bp

-

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.

signalword

Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

111.2 °F - closed cup

flash_point_c

44 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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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.
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)
Myrcene: a precursor of pheromones in Ips beetles.
P R Hughes
Journal of insect physiology, 20(7), 1274-1275 (1974-07-01)
E-myrcenol inIps duplicatus: An aggregation pheromone component new for bark beetles.
Byers JA, et al.
Experientia, 46(11-12), 1209-1211 (1990)
Johannes Stökl et al.
Proceedings. Biological sciences, 278(1709), 1216-1222 (2010-10-15)
Most insects are dependent on chemical communication for activities such as mate finding or host location. Several plants, and especially orchids, mimic insect semiochemicals to attract insects for unrewarded pollination. Here, we present a new case of pheromone mimicry found

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Protocols

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-β-Farnesene; α-Huµlene; Germacrene D; (+)-Valencene; Bicyclogermacrene; (+)-δ-Cadinene

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