M100005

Sigma-Aldrich

Myrcene

technical grade

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

Quality Level

grade

technical grade

vapor density

4.7 (vs air)

vapor pressure

~7 mmHg ( 20 °C)

contains

1000 ppm BHT as inhibitor

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.

Packaging

5, 100, 500 mL in glass bottle

signalword

Warning

hazcat

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

storage_class_code

3 - Flammable liquids

WGK Germany

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

Certificate of Analysis

Certificate of Origin

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)
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....
Flavia Bonamin et al.
Chemico-biological interactions, 212, 11-19 (2014-02-01)
The monoterpene β-myrcene has been widely used in cosmetics, food and beverages, and it is normally found in essential oil from citrus fruit. The aim of this study was to investigate the anti-ulcer effects of β-myrcene on experimental models of...
Protocols
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