123-35-3 Usage
Description
Different sources of media describe the Description of 123-35-3 differently. You can refer to the following data:
1. Myrcene has a pleasant odor. Prepared from linalool.
2. β-Myrcene is a terpene that has been found in Cannabis and has antioxidative properties. It reduces thiobarbituric acid reactive substance (TBARS) and increases glutathione (GSH), catalase, GSH peroxidase, and CuZn superoxide dismutase levels in a rat model of persistent environmental pollutant-induced oxidative stress when administered at a dose of 200 mg/kg per day.
Chemical Properties
Different sources of media describe the Chemical Properties of 123-35-3 differently. You can refer to the following data:
1. Myrcene has a pleasant, sweet, balsamic, plastic odor.
2. colourless viscous liquid
Occurrence
Reported found in Mircia acris D.C.; in the distillates from leaves of Rhus cotinus and Barosma venustum (52
and 43%, respectively); in lemongrass, cypress, artemisia; in the fruits of Phellodendron amurense (92%) and Phellodendron japonicum; in the oils of Picea balsamea, Tsuga canadenis, Abies balsamea, clary sage and others. Also reported in over 200 foods and
beverages including citrus peel oils and juices, apricot, sweet and sour cherry, berries, guava, pineapple, carrot, celery, potato, bell
pepper, black currants, anise, anise seed, cardamom, cinnamon, cassia, clove, capsicum varities, ginger, mentha oils, mace, parsley,
thyme, cheeses, cream, pork, hop oil, beer, white wine, rum, cocoa, coffee, tea, mango, tamarind, coriander, gin, sweet bay, prickly
pear, calamus, dill, lovage, caraway, buckwheat, corn, basil, fennel, kiwifruit, rosemary, myrtle berry, turmeric, lemon balm, sage,
pimento, angelica oil, Roman and German chamomile oil, eucalyptus and mastic gum oil
Uses
Different sources of media describe the Uses of 123-35-3 differently. You can refer to the following data:
1. Found in oil of bay, verbena, hop, etc. Used as an intermediate in the manufacturing of perfume chemicals.
2. 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.
Preparation
From linalool
Definition
ChEBI: A monoterpene that is octa-1,6-diene bearing methylene and methyl substituents at positions 3 and 7 respectively.
Aroma threshold values
Aroma characteristics at 10%: terpy, herbaceous, woody with a rosy celery and carrot nuance
Taste threshold values
Taste characteristics at 5 to 100 ppm: woody, vegetative, citrus fruity with a tropical mango and slight, leafy,
minty nuance
Synthesis Reference(s)
Journal of the American Chemical Society, 97, p. 3252, 1975 DOI: 10.1021/ja00844a073The Journal of Organic Chemistry, 47, p. 4161, 1982 DOI: 10.1021/jo00142a031Tetrahedron Letters, 25, p. 5193, 1984 DOI: 10.1016/S0040-4039(01)81561-6
General Description
A yellow oily liquid with a pleasant odor. Flash point below 200°F. Insoluble in water and less dense than water.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
The unsaturated aliphatic hydrocarbons, such as MYRCENE, are generally much more reactive than the alkanes. Strong oxidizers may react vigorously with them. Reducing agents can react exothermically to release gaseous hydrogen. In the presence of various catalysts (such as acids) or initiators, compounds in this class can undergo very exothermic addition polymerization reactions. Many of these compounds undergo autoxidation upon exposure to the air to form explosive peroxides. Violent explosions have occurred at low temperatures in ammonia synthesis gas units. These explosions have been traced to the addition products of dienes and oxides of nitrogen, produced from the interaction of nitrogen oxide and oxygen [Bretherick, 1995].
Health Hazard
May be harmful by inhalation, ingestion or skin absorption.
Fire Hazard
Special Hazards of Combustion Products: Vapor may travel considerable distance to a source of ignition and flashback.
Safety Profile
Low toxicity by
ingestion and skin contact. Experimental
reproductive effects. A moderate skin and
eye irritant. A flammable liquid. When
heated to decomposition it emits acrid
smoke and irritating fumes.
Check Digit Verification of cas no
The CAS Registry Mumber 123-35-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 3 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 123-35:
(5*1)+(4*2)+(3*3)+(2*3)+(1*5)=33
33 % 10 = 3
So 123-35-3 is a valid CAS Registry Number.
InChI:InChI=1/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7H,1,4,6,8H2,2-3H3
123-35-3Relevant articles and documents
-
Walker,Hawkins
, p. 4209 (1952)
-
Takabe,K. et al.
, p. 2662 (1972)
Naves,Bondavalli
, p. 563 (1965)
Molybdenum- and tungsten-catalyzed allylation of aromatic compounds with allylic esters and alcohols
Shimizu, Isao,Sakamoto, Toshiaki,Kawaragi, Saeko,Maruyama, Yooichiro,Yamamoto, Akio
, p. 137 - 138 (1997)
A novel method to substitute aromatic compounds with allylic groups using oxygen-containing allylic compounds in the presence of molybdenum or tungsten carbonyls under neutral conditions has been developed. The method is applicable to one step synthesis of methyl eugenol.
-
Haley et al.
, p. 264 (1969)
-
Selective Synthesis of 1,3-Dienic Terpenes in a β-Form through Regioselective 1,4-Elimination of Allylic Ethers
Otera, Junzo,Niibo, Yoshihisa,Okuda, Kazuhiro
, p. 1829 - 1832 (1986)
γ-Methyl-substituted allylic ethers proved to be converted into β-substituted dienes exclusively on treatment with t-BuOK in refluxing THF or cyclohexane.
Flash vacuum thermolysis of terpenic compounds in the pinane series
Lemee,Ratier,Duboudin,Delmond
, p. 1313 - 1318 (1995)
The flash pyrolysis of various derivatives (hydrocarbons and oxygenated compounds) in the pinane series has been studied. We observed a high degree of conversion and good selectivity.
Mochida
, p. dtsch.Ref.S.133 (1934)
-
Tanaka,S. et al.
, p. 3252 - 3254 (1975)
-
-
Hunt,Hawkins
, p. 5618 (1950)
-
Thermal behavior of pinan-2-ol and linalool
Leiner, Janne,Stolle, Achim,Ondruschka, Bernd,Netscher, Thomas,Bonrath, Werner
, p. 8358 - 8375 (2013)
Linalool is an important intermediate for syntheses of isoprenoid fragrance compounds and vitamins A and E. One process option for its production is the thermal gas-phase isomerization of cis- and trans-pinan-2-ol. Investigations of this reaction were performed in a flow-type apparatus in a temperature range from 350-600 °C and a residence time range of 0.6-0.8 s. Rearrangement of the bicyclic alcohol led to linalool, plinols arising from consecutive reactions of linalool and other side products. Effects of residence time, temperature, surface-to-volume-ratio, carrier gas, and the presence of additives on yield and selectivity were studied. Furthermore, the effects of such parameters on ene-cyclization of linalool affording plinols were investigated. Results indicate that manipulation of the reaction in order to affect selectivity is difficult due to the large free path length to other molecules in the gas phase. However, conditions have been identified allowing one to increase the selectivity and the yield of linalool throughout pyrolysis of pinan-2-ol.
Hawkins,Vogh
, p. 902 (1953)
Preparation method of myrcene
-
Paragraph 0043-0044, (2021/11/19)
The method uses geraniol and/or nerol and/or linalool as a raw material, uses a palladium source and an organic phosphine as a catalyst to prepare myrcene, and realizes chemical synthesis of myrcene. The method has the advantages of high catalytic efficiency and high product selectivity.
Method for synthesizing high-purity 13C2-myrcene from 13C2-geraniol
-
, (2020/08/06)
The invention relates to a method for synthesizing high-purity 13C2-myrcene from 13C2-geraniol. The method comprises the following steps: (1) dissolving 13C2-geraniol in an organic solvent, adding hydrogen peroxide and p-toluenesulfonic acid monohydrate, stirring for reaction, monitoring the reaction process by TLC (Thin Layer Chromatography), after the reaction is completed, concentrating the obtained reaction solution under reduced pressure, and purifying by silica gel column chromatography to obtain an intermediate, (2) dissolving the intermediate in an organic solvent, stirring and heatingto react with potassium tert-butoxide and 18-crown ether-6 dissolved in an organic solvent under the protection of nitrogen, by TLC, monitoring the reaction process, after the reaction is completed,stirring and cooling the obtained reaction liquid, adding diethyl ether for extraction, sequentially cleaning an organic phase with water, a saturated sodium bicarbonate aqueous solution and saturatededible salt water, carrying out drying, and carrying out silica gel column chromatography purification so that high-purity 13C2-myrcene is obtained. According to the method, no metal catalyst or additive is used, the process conditions are mild, and the method has the advantages of being simple, efficient, economical and environmentally friendly and is particularly suitable for synthesis of isotope 13C or 14C labeled myrcene and non-isotope labeled myrcene.