Myrcene

Myrcene

Names
IUPAC name 7-Methyl-3-methylene-1,6-octadiene
Identifiers
CAS Number	123-35-3 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17221 N
ChEMBL	ChEMBL455491 Y
ChemSpider	28993 Y
ECHA InfoCard	100.004.203
KEGG	C06074 Y
PubChem	31253
InChI InChI=1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7H,1,4,6,8H2,2-3H3 Y Key: UAHWPYUMFXYFJY-UHFFFAOYSA-N Y InChI=1/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7H,1,4,6,8H2,2-3H3 Key: UAHWPYUMFXYFJY-UHFFFAOYAT
SMILES CC(=CCCC(=C)C=C)C
Properties
Chemical formula	C10H16
Molar mass	136.24 g·mol−1
Density	0.794 g/cm3
Melting point	< −10 °C (14 °F; 263 K)
Boiling point	166 to 168 °C (331 to 334 °F; 439 to 441 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Myrcene, or β-myrcene, is an olefinic natural organic hydrocarbon. It is more precisely classified as a monoterpene. Monoterpenes are dimers of isoprenoid precursors, and myrcene is one of the most important. It is a component of the essential oil of several plants including bay, cannabis, ylang-ylang, wild thyme, parsley, and hops. It is produced mainly semi-synthetically from myrcia, from which it gets its name. It is a key intermediate in the production of several fragrances. α-Myrcene is the name for the structural isomer 2-methyl-6-methylene-1,7-octadiene, which is not found in nature and is little used.

Terpenes arise naturally from dehydration of terpenol geraniol. It could in principle be extracted from any number of plants, for example wild thyme, the leaves of which contain up to 40% by weight of myrcene. The current route to commercial samples is by the pyrolysis (400 °C) of β-pinene, which is obtained from turpentine.

Myrcene is an important intermediate used in the perfumery industry. It has a pleasant odor, but is rarely used directly. It is also unstable in air, tending to polymerize. Samples are stabilized by the addition of alkylphenols or . It is thus more highly valued as an intermediate for the preparation of flavor and fragrance chemicals such as menthol, citral, citronellol, citronellal, geraniol, nerol, and linalool. Treatment of myrcene with hydrogen chloride gives geranyl chloride, neryl chloride, and linalyl chloride. Treatment of these compounds with acetic acid gives geranyl acetate, neryl acetate, and linalyl acetate, respectively. These esters are then hydrolyzed to the corresponding alcohols. Myrcene is also converted to myrcenol, another fragrance found in lavender, via uncatalyzed hydroamination of the 1,3-diene followed by hydrolysis and Pd-catalyzed removal of the amine.