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Myrcene
[CAS# 123-35-3]

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Identification
ClassificationFlavors and spices >> Synthetic spice >> Hydrocarbon spice >> Olefin
NameMyrcene
Synonyms7-Methyl-3-methylene-1,6-octadiene
Molecular StructureCAS # 123-35-3, Myrcene
Molecular FormulaC10H16
Molecular Weight136.24
CAS Registry Number123-35-3
EC Number204-622-5
FEMA2762
SMILESCC(=CCCC(=C)C=C)C
Properties
Water solubilitypractically insoluble
Density0.8±0.1 g/cm3, Calc.*, 0.79 g/mL (20 °C) (Expl.)
Melting point<-80 °C °C (Expl.)
Index of Refraction1.450, Calc.*, 1.460 (Expl.)
Boiling Point167.0±0.0 °C (760 mmHg), Calc.*, 167 °C (Expl.)
Flash Point39.4±0.0 °C, Calc.*, 44 °C (Expl.)
*Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Symbolssymbol symbol symbol symbol   GHS02;GHS07;GHS08;GHS09 Danger  Details
Risk StatementsH226-H304-H315-H319-H400-H412  Details
Safety StatementsP210-P233-P240-P241-P242-P243-P264-P264+P265-P273-P280-P301+P316-P302+P352-P303+P361+P353-P305+P351+P338-P321-P331-P332+P317-P337+P317-P362+P364-P370+P378-P391-P403+P235-P405-P501  Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Flammable liquidsFlam. Liq.3H226
Aspiration hazardAsp. Tox.1H304
Skin irritationSkin Irrit.2H315
Eye irritationEye Irrit.2H319
Chronic hazardous to the aquatic environmentAquatic Chronic3H412
Acute hazardous to the aquatic environmentAquatic Acute1H400
Chronic hazardous to the aquatic environmentAquatic Chronic2H411
Skin sensitizationSkin Sens.1BH317
Chronic hazardous to the aquatic environmentAquatic Chronic1H410
Skin sensitizationSkin Sens.1H317
Specific target organ toxicity - single exposureSTOT SE3H335
Specific target organ toxicity - single exposureSTOT SE3H336
Chronic hazardous to the aquatic environmentAquatic Chronic2H412
Transport InformationUN 2319
SDSAvailable
up Discovery and Applications
Myrcene is a naturally occurring terpene and one of the most abundant compounds found in the essential oils of various plants, including hops, bay leaves, and lemongrass. It is a colorless liquid with a distinct earthy, musky odor, and it is classified as a monoterpene, which is a class of terpenes containing ten carbon atoms. Myrcene is significant in both the fragrance and flavor industries, as well as in the production of certain bio-based chemicals.

The discovery of myrcene dates back to the early 19th century, with its isolation from the essential oil of bay laurel. The compound’s structure was determined later in the 20th century, as the understanding of terpene chemistry advanced. Myrcene has since become one of the most studied terpenes due to its widespread occurrence in nature and its potential applications in various industries.

In the fragrance industry, myrcene is valued for its musky, earthy scent, which is often described as similar to cloves or hops. It is commonly used in perfumes, cosmetics, and other scented products to provide depth and complexity to the fragrance profile. Its presence is especially prominent in perfumes with woody or herbal notes, and it is often included in compositions that evoke natural, botanical aromas. Myrcene is also used in the production of essential oils and can be found in mixtures used for aromatherapy and massage oils.

Beyond its use in fragrances, myrcene is also a key component of the flavor profile of many food and beverage products. It imparts a pleasant, spicy, and slightly citrus-like flavor, making it useful in the flavoring of beverages, confectioneries, and even some savory foods. Myrcene contributes to the characteristic flavor of hops and is one of the compounds responsible for the aroma and taste of beer, particularly in hop-forward styles like India Pale Ales (IPAs).

In addition to its applications in flavor and fragrance, myrcene has been studied for its potential medicinal properties. Research has shown that myrcene possesses analgesic, anti-inflammatory, and sedative effects, which may make it useful in the development of therapeutic products. Some studies have suggested that myrcene can have a synergistic effect when combined with other compounds, such as cannabinoids, in products designed for pain relief or relaxation.

Myrcene is also utilized in the synthesis of other chemicals, including the production of limonene, a terpene used widely in the cleaning and fragrance industries. Myrcene can undergo chemical reactions, such as cyclization, to yield a variety of products used in industrial applications, including as solvents and intermediates in the synthesis of plastics and other materials.

In conclusion, myrcene is an important natural compound with a broad range of applications across industries such as fragrance, food and beverage, and pharmaceuticals. Its distinct odor and flavor properties make it valuable in perfumery and flavoring, while its potential therapeutic effects contribute to ongoing research into its medicinal uses. Myrcene also plays a role in the synthesis of other valuable terpenes and chemicals, further emphasizing its versatility in both natural and industrial chemistry.

References

2024. Aquaphotomics study of fresh cannabis inflorescence: near infrared spectral analysis of water matrix structures. Analytical and Bioanalytical Chemistry.
DOI: 10.1007/s00216-024-05685-z

2009. Study on selectivity of β-myrcene hydrogenation in high-pressure carbon dioxide catalysed by noble metal catalysts. Green Chemistry, 11(11).
DOI: 10.1039/b916017p

2003. Hydroformylation of myrcene: metal and ligand effects in the hydroformylation of conjugated dienes. New Journal of Chemistry, 27(3).
DOI: 10.1039/b207947j
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