123-35-3

Basic information

• Product Name: Myrcene
• Synonyms: Myrcene technical grade;Myrcene CAS;BETA-MYRCENE;FEMA 2762;7-METHYL-3-METHYLEN-1,6-OCTADIENE;7-METHYL-3-METHYLENE-1,6-OCTADIENE;OIL;MYRCENE
• CAS NO: 123-35-3
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23
• EINECS: 204-622-5
• Product Categories: Aroma Chemicals;Aliphatics;Acyclic;Alkenes;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 123-35-3.mol
• Article Data: 65

Chemical Properties

• Melting Point: <-10 °C
• Boiling Point: 167 °C(lit.)
• Flash Point: 103 °F
• Appearance: Clear light yellow/Viscous Liquid
• Density: 0.791 g/mL at 25 °C(lit.)
• Vapor Density: 4.7 (vs air)
• Vapor Pressure: ~7 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.469(lit.)
• Storage Temp.: 2-8°C
• Solubility: water: soluble0.00109g/L at 20°C
• Water Solubility: practically insoluble
• Stability: Unstable - may be inhibited by the addition of ca. 400 ppm tenox GT-1 or 1000 ppm BHT. Flammable. Incompatible with strong oxidi
• Merck: 14,6331
• BRN: 1719990
• CAS DataBase Reference: Myrcene(CAS DataBase Reference)
• NIST Chemistry Reference: Myrcene(123-35-3)
• EPA Substance Registry System: Myrcene(123-35-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 10-36/37/38-R36/37/38-R10-65-38
• Safety Statements: 16-26-36-37/39-S37/39-S26-S16-62
• RIDADR: UN 2319 3/PG 3
• WGK Germany: 2
• RTECS: RG5365000
• F: 10-23
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 123-35-3(Hazardous Substances Data)

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.

InChI:InChI=1/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7H,1,4,6,8H2,2-3H3

Synthetic route

(2-methylene-3-butenyl)-trimethyltin (71092-51-8) + prenyl bromide (870-63-3) → 7-methyl-3-methene-1,6-octadiene (123-35-3)

Conditions	Yield
With zinc(II) chloride In tetrahydrofuran at 65℃;	94%

2-chloromethyl-1,3-butadiene (4075-28-9) + 3-methyl-2-butenylmagnesium chloride (35189-96-9) → 7-methyl-3-methene-1,6-octadiene (123-35-3)

Conditions	Yield
In tetrahydrofuran at 0℃; for 10h;	92%

neryl acetate (141-12-8) → 7-methyl-3-methene-1,6-octadiene (123-35-3)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); 2-Propynylzinc bromide In tetrahydrofuran for 3h; Ambient temperature;	90%

geranyl 2-tetrahydropyranyl ether (59632-99-4) → 7-methyl-3-methene-1,6-octadiene (123-35-3)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran for 6h; Heating;	89%
With 18-crown-6 ether; potassium tert-butylate In tetrahydrofuran at 60℃; for 12h; Inert atmosphere;	73.1%

O-(trans-3,7-dimethylocta-2,6-dien-1-yl)trimethylsilane (72106-90-2) → 7-methyl-3-methene-1,6-octadiene (123-35-3)

Conditions	Yield
With tetrahydrofuran; lithium diisopropylamide at -78℃; for 5h;	85%

neryl 2-tetrahydropyranyl ether (70473-31-3) → 7-methyl-3-methene-1,6-octadiene (123-35-3)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran for 18h; Heating;	83%

geraniol methyl ether (2565-83-5, 72152-72-8, 2565-82-4) → 7-methyl-3-methene-1,6-octadiene (123-35-3)

Conditions	Yield
With potassium tert-butylate; 18-crown-6 ether In tetrahydrofuran for 2h; Heating;	76%

(2Z)-1-methoxy-3,7-dimethylocta-2,6-diene (2565-83-5) + LIDAKOR → 7-methyl-3-methene-1,6-octadiene (123-35-3)

Conditions	Yield
In tetrahydrofuran at -50℃; for 1h;	76%

4-methyl-3-pentenylmagnesium bromide (37586-57-5) + buta-2,3-dien-1-yl diethyl phosphate (89228-81-9) → 7-methyl-3-methene-1,6-octadiene (123-35-3)

Conditions	Yield
In tetrahydrofuran for 0.5h; Ambient temperature;	75%

beta-pinene (18172-67-3, 19902-08-0) → 7-methyl-3-methene-1,6-octadiene (123-35-3) + pseudolimonene (499-97-8) + (-)-(S)-limonene (5989-54-8)

Conditions	Yield
In ethanol at 400℃; under 91206.1 Torr; for 0.0194444h; Product distribution; Further Variations:; Temperatures;	A 72% B 8% C n/a

geraniol methyl ether (2565-83-5, 72152-72-8, 2565-82-4) + LIDAKOR → 7-methyl-3-methene-1,6-octadiene (123-35-3)

Conditions	Yield
In tetrahydrofuran at -30℃; for 15h;	66%

6-Methyl-2-(toluene-4-sulfonyl)-2-vinyl-hept-5-en-1-ol (79240-18-9) → 7-methyl-3-methene-1,6-octadiene (123-35-3)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 2h; Heating;	62%

4,4,4-Trifluoro-3-oxo-butyric acid (E)-3,7-dimethyl-octa-2,6-dienyl ester (125061-34-9) → 7-methyl-3-methene-1,6-octadiene (123-35-3) + 1,1,1-trifluoro-6,10-dimethyl-undeca-5,9-dien-2-one (118453-57-9)

Conditions	Yield
tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran Heating;	A n/a B 56%

(E)-N,N-diethyl-3,7-dimethyl-2,6-octadienylamine (40267-53-6) → 7-methyl-3-methene-1,6-octadiene (123-35-3)

Conditions	Yield
at 130℃; under 20 Torr; for 5h;	50%

2-(geranyloxy)-3,5,7-trimethyltropone → 7-methyl-3-methene-1,6-octadiene (123-35-3) + (Z)-ocimene (3338-55-4) + trans ocimene (3779-61-1) + 3,5,7-trimethyltropolone (2885-58-7)

Conditions	Yield
at 180℃; pyrolysis;	A 30% B 8% C 49% D n/a
at 140℃; pyrolysis;	A 23% B 12% C 36% D n/a

geranyl phenyl sulfide (35162-74-4) + acetic anhydride (108-24-7) + acetic acid (64-19-7) → 7-methyl-3-methene-1,6-octadiene (123-35-3) + 3,7-dimethyl-2E,6-octadien-1-yl acetate (105-87-3) + (Z)-ocimene (3338-55-4)

Conditions	Yield
With lithium acetate; copper diacetate; copper at 85 - 90℃;	A n/a B 43% C n/a

phthalimide (136918-14-4) + (E)-7-methylocta-5,7-dien-1-yl 4-methylbenzenesulfonate → 7-methyl-3-methene-1,6-octadiene (123-35-3)

Conditions	Yield
With 18-crown-6 ether In N,N-dimethyl-formamide at 100℃; for 16h;	43%

(2Z)-1-methoxy-3,7-dimethylocta-2,6-diene (2565-83-5) → 7-methyl-3-methene-1,6-octadiene (123-35-3)

Conditions	Yield
With potassium tert-butylate; 18-crown-6 ether In tetrahydrofuran for 7h; Heating;	35%

2-(geranyl-oxy)tropone → 7-methyl-3-methene-1,6-octadiene (123-35-3) + 5-(3,7-dimethyl-2,6-octadienyl)tropolone (83849-32-5) + 3-(1,5-dimethyl-1-vinyl-4-hexenyl)tropolone

Conditions	Yield
at 140℃; for 2h; pyrolysis; Further byproducts given;	A 3 % Chromat. B 32% C 31%

2-(geranyl-oxy)tropone → 7-methyl-3-methene-1,6-octadiene (123-35-3) + 5-(3,7-dimethyl-2,6-octadienyl)tropolone (83849-32-5) + 3-(1,5-dimethyl-1-vinyl-4-hexenyl)tropolone + isoprene (78-79-5)

Conditions	Yield
at 140℃; for 2h; pyrolysis; Further byproducts given;	A 3 % Chromat. B 32% C 31% D 10 % Chromat.

isoprene (78-79-5) → 7-methyl-3-methene-1,6-octadiene (123-35-3)

Conditions	Yield
	32%
	23%
In tetrahydrofuran	15%
With sodium; N-cyclohexyl-cyclohexanamine In tetrahydrofuran Mechanism; K, Li various dialkylamines;
In tetrahydrofuran at 10℃; Rate constant; Na, dicyclohexylamine;

geranyl methyl carbonate (85217-72-7) → 7-methyl-3-methene-1,6-octadiene (123-35-3) + (Z)-ocimene (3338-55-4)

Conditions	Yield
With hexacarbonyl molybdenum In toluene at 110℃; for 72h;	A 7% B 31%

3,7-dimethyl-oct-6-enal (106-23-0, 26489-02-1) → 7-methyl-3-methene-1,6-octadiene (123-35-3) + 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) + 1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) + 3,8-p-Menthadien (586-67-4) + limonene. (138-86-3)

Conditions	Yield
With aluminum oxide; carbon dioxide In hexane at 190℃; Supercritical conditions;	A 15.8% B 6.2% C 11.9% D 30.8% E 5.2%

3,5,7-trimethyl-2-(neryloxy)tropone → 7-methyl-3-methene-1,6-octadiene (123-35-3) + (Z)-ocimene (3338-55-4) + trans ocimene (3779-61-1)

Conditions	Yield
at 140℃;	A 29% B 9% C 27%
at 140℃; pyrolysis;	A 29% B 9% C 27%

Geraniol (106-24-1) → 7-methyl-3-methene-1,6-octadiene (123-35-3) + (Z)-ocimene (3338-55-4) + trans ocimene (3779-61-1) + Terpinolene (586-62-9) + limonene. (138-86-3)

Conditions	Yield
With tin(ll) chloride In dimethyl sulfoxide at 139.84℃; for 2h;	A 27% B 24% C 17% D 10% E 22%

Geraniol (106-24-1) → 7-methyl-3-methene-1,6-octadiene (123-35-3)

Conditions	Yield
With copper(II) sulfate In neat (no solvent) at 125℃; under 25 Torr; for 1.5h;	25%
Multi-step reaction with 3 steps 1: 86 percent 2: NaI / acetone / 1 h / 0 - 2 °C 3: triethylamine / hexane / 6 h / 25 °C / Irradiation View Scheme
With bis(acetylacetonato)palladium(II); carbon monoxide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; trifluoroacetic acid In toluene at 105℃; under 30003 Torr; for 18h; chemoselective reaction;
Multi-step reaction with 2 steps 1: Castellaniella defragrans linalool dehydratase isomerase / 20 h / Enzymatic reaction 2: Castellaniella defragrans linalool dehydratase isomerase / 20 h / Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C 2: potassium tert-butylate; 18-crown-6 ether / tetrahydrofuran / 12 h / 60 °C / Inert atmosphere View Scheme

3,7-dimethyl-oct-6-enal (106-23-0, 26489-02-1) → 7-methyl-3-methene-1,6-octadiene (123-35-3) + 1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) + 3,8-p-Menthadien (586-67-4) + 3-p-menthene (500-00-5) + (+/-)-menthone (491-07-6, 1074-95-9, 1196-31-2, 3391-87-5, 10458-14-7, 14073-97-3, 18309-28-9, 36977-92-1, 117773-78-1, 89-80-5)

Conditions	Yield
With aluminum oxide; carbon dioxide In hexane at 190℃; Supercritical conditions;	A 6.9% B 8.2% C 21.4% D 6.3% E 6.6%

2-(geranyl-oxy)tropone → 7-methyl-3-methene-1,6-octadiene (123-35-3) + (Z)-ocimene (3338-55-4) + trans ocimene (3779-61-1) + 3-(1,5-dimethyl-1-vinyl-4-hexenyl)tropolone

Conditions	Yield
at 180℃; for 15h; Further byproducts given;	A 15% B 6% C 19% D n/a
at 180℃; for 0.25h; pyrolysis; Further byproducts given;	A 15% B 6% C 19% D n/a
at 180℃; for 15h; pyrolysis; Further byproducts given;	A 15 % Chromat. B 6 % Chromat. C 19 % Chromat. D n/a

tert-butylamine (75-64-9) + diisopropylamine (108-18-9) + isoprene (78-79-5) → 7-methyl-3-methene-1,6-octadiene (123-35-3)

Conditions	Yield
	18.6%

formaldehyd (50-00-0) + 7-methyl-3-methene-1,6-octadiene (123-35-3) + ethyl acetoacetate (141-97-9) → ethyl 1-acetyl-4-(4-methylpent-3-en-1-yl)cyclohex-3-enecarboxylate

Conditions	Yield
With zinc(II) chloride In tetrahydrofuran at 70℃; for 48h; Diels-Alder Cycloaddition; Sealed tube;	100%

7-methyl-3-methene-1,6-octadiene (123-35-3) + acrylic acid methyl ester (292638-85-8) → 1(4-methyl-3-pentenyl)-4-carbmethoxy-cyclohex-1-ene (53311-89-0)

Conditions	Yield
With K10 supported ecological catalyst (0.1equiv. Zn) In toluene at 110℃; for 1h;	99%
silica gel at 100℃; for 4h;	60%

7-methyl-3-methene-1,6-octadiene (123-35-3) + trans-1,2-cyclohexandiol (1460-57-7) → (4aRS,8aSR)-6-(4-methylpent-3-en-1-yl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene-4a,8a-diol

Conditions	Yield
With dodecacarbonyl-triangulo-triruthenium; 1,3-bis-(diphenylphosphino)propane In toluene at 130℃; for 48h; Inert atmosphere;	99%
With dodecacarbonyl-triangulo-triruthenium; 2,2'-bis(diphenylphosphino)biphenyl In toluene at 130℃; for 48h; Inert atmosphere; diastereoselective reaction;	84%

7-methyl-3-methene-1,6-octadiene (123-35-3) + 1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one (1214-47-7) → (2-hydroxyphenyl)((1R,2R)-5-(4-methylpent-3-en-1-yl)-1,2,3,6-tetrahydro-[1,1'-biphenyl]-2-yl)methanone

Conditions	Yield
Stage #1: 1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one With borane-THF; (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol; acetic acid In tetrahydrofuran at 20℃; for 1h; Diels-Alder Cycloaddition; Molecular sieve; Inert atmosphere; Stage #2: 7-methyl-3-methene-1,6-octadiene In tetrahydrofuran at 20℃; for 12h; Diels-Alder Cycloaddition; Molecular sieve; Inert atmosphere; enantioselective reaction;	99%
Stage #1: 1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one With triphenylborane; (S)-2,15-dichlorotetraphenylene-1,16-diol In 1,2-dichloro-ethane at 100℃; for 2h; Diels-Alder Cycloaddition; Inert atmosphere; Schlenk technique; Sealed tube; Molecular sieve; Stage #2: 7-methyl-3-methene-1,6-octadiene In 1,2-dichloro-ethane at 30℃; Diels-Alder Cycloaddition; Inert atmosphere; Schlenk technique; Sealed tube; Molecular sieve; stereoselective reaction;	89%

7-methyl-3-methene-1,6-octadiene (123-35-3) + ethyl 2-((2-oxo-2-phenylethyl)thio)acetate (66560-19-8) → C14H22O2S

Conditions	Yield
In dichloromethane at -10℃; for 0.5h; Inert atmosphere; UV-irradiation; Flow reactor; regioselective reaction;	99%

7-methyl-3-methene-1,6-octadiene (123-35-3) → 2,6-dimethyloctane (2051-30-1)

Conditions	Yield
With nickel(II) bis(octanoate); hydrogen; 1,4-bis(2,6-diisopropylphenyl)-2,3-dimethyl-1,4-diazabuta-1,3-diene; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In benzene-d6 at 50℃; under 3040.2 Torr; for 24h; Reagent/catalyst;	98%
With cobalt In tetrahydrofuran Heating; High pressure;	79%
With 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthenecobalt(II) dibromide; hydrogen; lithium triethylborohydride In tetrahydrofuran at 20℃; under 7500.75 Torr; for 24h;	76%

7-methyl-3-methene-1,6-octadiene (123-35-3) + PVS (5535-48-8) → [4-(4-Methyl-pent-3-enyl)-cyclohex-3-enesulfonyl]-benzene (73301-16-3)

Conditions	Yield
In benzene at 155℃; for 22h;	98%
With hydroquinone In benzene at 155℃; for 22h;	88.6%

7-methyl-3-methene-1,6-octadiene (123-35-3) → 6,7-epoxymyrcene (29414-55-9)

Conditions	Yield
With dihydrogen peroxide; tungsten(VI) oxide; [CH3(n-C8H17)3N]+H2PO4- In toluene at 21℃; for 3h;	98%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 22℃; for 0.0833333h;	97%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 0.0833333h; cooling;	95.2%

7-methyl-3-methene-1,6-octadiene (123-35-3) → 3-(4-methylpent-3-en-1-yl)-2,5-dihydrothiophene-1,1-dioxide (2083-32-1)

Conditions	Yield
Stage #1: 7-methyl-3-methene-1,6-octadiene With 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate In acetonitrile at 20℃; Inert atmosphere; Sealed tube; Stage #2: With boron trifluoride diethyl etherate In acetonitrile at 0 - 70℃; for 12h; Inert atmosphere; Sealed tube;	97%
With sodium metabisulfite; 1,1,1,3',3',3'-hexafluoro-propanol In water at 100℃; under 517.162 - 1034.32 Torr; for 14h; Reagent/catalyst; Sealed tube;	86%
With diethyl ether; sulfur dioxide at 100℃;

7-methyl-3-methene-1,6-octadiene (123-35-3) + 1-benzyl-3-hydroxy-5-methoxyindolin-2-one (1439598-96-5) → (E)-1-benzyl-3-(3,7-dimethylocta-2,6-dien-1-yl)-3-hydroxy-5-methoxyindolin-2-one (1439599-39-9)

Conditions	Yield
With dodecacarbonyl-triangulo-triruthenium; tricyclohexylphosphine In toluene at 110℃; for 48h; Inert atmosphere; Sealed tube; regioselective reaction;	97%

7-methyl-3-methene-1,6-octadiene (123-35-3) + E-1-(4'-methoxyphenyl)prop-1-ene (4180-23-8) → (±)-(1S,2S)-4'-methoxy-2-methyl-4-(4-methylpent-3-en-1-yl)-1,2,3,6-tetrahydro-1,1'-biphenyl

Conditions	Yield
With iron perchlorate hexahydrate In acetonitrile at 20℃; for 24h; Diels-Alder Cycloaddition; regioselective reaction;	97%
With C26H18N10Ru(2+)*2C32H12BF24(1-) In dichloromethane for 1.5h; Diels-Alder Cycloaddition; Irradiation;	88%
With 9-(2-trifluoromethylphenyl)-1,3,6,8-tetramethoxythioxanthylium trifluoromethanesulfonate In nitromethane at 20℃; for 1h; Diels-Alder Cycloaddition; UV-irradiation;	84%
With iron(III) chloride In dichloromethane; acetonitrile at 0℃; for 3h;	76%

methanol (67-56-1) + 7-methyl-3-methene-1,6-octadiene (123-35-3) → 6-Bromo-7-methoxy-7-methyl-3-methylene-oct-1-ene (76280-53-0)

Conditions	Yield
With N-Bromosuccinimide; sulfuric acid In 1,4-dioxane Ambient temperature;	96%

7-methyl-3-methene-1,6-octadiene (123-35-3) + 4-Methoxybenzyl alcohol (105-13-5) → 1-(4-methoxyphenyl)-2,7-dimethyl-3-methyleneoct-6-en-1-one (1072266-04-6)

Conditions	Yield
With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II); trifluoroacetic acid In toluene at -78 - 110℃; Inert atmosphere; regioselective reaction;	96%

7-methyl-3-methene-1,6-octadiene (123-35-3) + carbon monoxide (201230-82-2) + benzyl alcohol (100-51-6) → C18H24O2

Conditions	Yield
With dichloro(1,5-cyclooctadiene)palladium(II); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 100℃; under 30003 - 67506.8 Torr; for 20h; Inert atmosphere; Autoclave;	96%

7-methyl-3-methene-1,6-octadiene (123-35-3) + 1,2-bis-(p-methylphenylsulfonamido)-benzene (49633-28-5) → 2-(6-methylhepta-1,5-dien-2-yl)-1,4-Ditosyl-1,2,3,4-tetrahydroquinoxaline

Conditions	Yield
With oxygen; palladium diacetate In acetonitrile at 70℃; under 760.051 Torr; for 48h; Sealed tube; Molecular sieve; chemoselective reaction;	96%

7-methyl-3-methene-1,6-octadiene (123-35-3) + phenylsilane (694-53-1) → C16H24Si

Conditions	Yield
With [(2,6-iPr2PhBDI)Mn(μ-H)]2 In benzene-d6 at 130℃; for 48h; Inert atmosphere;	96%

7-methyl-3-methene-1,6-octadiene (123-35-3) → (1Z,5Z)-1,6-bis(4-methylpent-3-en-1-yl)cycloocta-1,5-diene (58940-08-2)

Conditions	Yield
With [(MePI)FeCl(μ-Cl)]2; (butadiene)magnesium(THF)2 In neat (no solvent) at 23℃; for 3h; Reagent/catalyst; Inert atmosphere; Glovebox; Sealed tube; regioselective reaction;	96%

diazomethane (186581-53-3, 908094-01-9) + 7-methyl-3-methene-1,6-octadiene (123-35-3) → 2-cyclopropyl-6-methyl-1,5-heptadiene

Conditions	Yield
Stage #1: 7-methyl-3-methene-1,6-octadiene With benzophenone In diethyl ether at 20℃; Stage #2: diazomethane In diethyl ether at 20 - 35℃; for 1.5h;	95.19%

diiron nonacarbonyl (15321-51-4) + 7-methyl-3-methene-1,6-octadiene (123-35-3) → (η4-myrcene)tricarbonyliron (33434-20-7)

Conditions	Yield
In benzene Sonication; addn. of 1.1 equivalents of Fe2(CO)9 to a soln. of the diene in benzene, sonication for 1h or until all solid Fe2(CO)9 had disappeared, concn. of the soln.;; chromatography (SiO2, eluation with petroleum ether/ether);	95%

7-methyl-3-methene-1,6-octadiene (123-35-3) + ethene (74-85-1) → (Z)-2-methyl-6-(3-propenyl)-octa-2,6-diene (1215227-17-0)

Conditions	Yield
With CoCl2(1,4-bis(diphenylphosphino)butane); trimethylaluminum In dichloromethane; toluene at 0℃; under 760.051 Torr; for 6h; Reagent/catalyst; regioselective reaction;	95%
With C30H40FeN2 In pentane at 23℃; for 6h; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;	92%
With CoCl2(1,4-bis(diphenylphosphino)butane); trimethylaluminum In dichloromethane; toluene at 0℃; under 760.051 Torr; for 0.0833333h; Inert atmosphere;	97.1 mg

5-Methylfurfural (620-02-0) + 7-methyl-3-methene-1,6-octadiene (123-35-3) → C16H22O2

Conditions	Yield
With carbonyldihydridotris(triphenylphosphine)ruthenium(II); trifluoroacetic acid In toluene at 110℃; for 18h; Schlenk technique;	95%

allylbenzene (300-57-2) + 7-methyl-3-methene-1,6-octadiene (123-35-3) → C19H26

Conditions	Yield
With C37H47FeN5 at 23℃; for 48h; Diels-Alder Cycloaddition; stereoselective reaction;	95%

7-methyl-3-methene-1,6-octadiene (123-35-3) + 4-bromo-2'-hydroxylchalcone (65786-14-3, 16635-18-0) → C25H27BrO2

Conditions	Yield
Stage #1: 4-bromo-2'-hydroxylchalcone With (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol; α,α,α-trifluorotoluene; triphenylborane at 100℃; for 1h; Stage #2: 7-methyl-3-methene-1,6-octadiene for 9h; Reflux; enantioselective reaction;	95%

7-methyl-3-methene-1,6-octadiene (123-35-3) + [1,4]naphthoquinone (130-15-4) → 2-(4-methyl-3-pentenyl)-anthraquinone

Conditions	Yield
In toluene at 50℃; for 144h;	94%

7-methyl-3-methene-1,6-octadiene (123-35-3) + 1-benzyl-3-hydroxy-5-methylindolin-2-one (1366042-95-6) → (E)-1-benzyl-3-(3,7-dimethylocta-2,6-dien-1-yl)-3-hydroxy-5-methylindolin-2-one (1439599-37-7)

Conditions	Yield
With dodecacarbonyl-triangulo-triruthenium; tricyclohexylphosphine In toluene at 110℃; for 48h; Inert atmosphere; Sealed tube; regioselective reaction;	94%

5-phenylfuran-2-carbaldehyde (13803-39-9) + 7-methyl-3-methene-1,6-octadiene (123-35-3) → C21H24O2

Conditions	Yield
With carbonyldihydridotris(triphenylphosphine)ruthenium(II); trifluoroacetic acid In toluene at 110℃; for 18h; Schlenk technique;	94%

7-methyl-3-methene-1,6-octadiene (123-35-3) + diphenylsilane (775-12-2) → (7-methyl-3-methyleneoct-6-en-1-yl)diphenylsilane

Conditions	Yield
With C28H32N2; sodium triethylborohydride; iron(II) chloride In tetrahydrofuran at 20 - 40℃; for 2h; Inert atmosphere; Sealed tube; regioselective reaction;	94%

7-methyl-3-methene-1,6-octadiene (123-35-3) → 3-(4'-methyl-3'-pentenyl)-2,5-dihydrothiophene 1-oxide

Conditions	Yield
With naphthalene-1,8-trisulfide-2-oxide In chlorobenzene for 6h; Heating;	93%
With bicyclo[3.3.1]nonylidenebicyclo[3.3.1]nonanethiirane 1-oxide In toluene Cycloaddition; Heating;	68%
With dimethyl acetylenedicarboxylate In dichloromethane at 20℃; for 0.5h;	27%

7-methyl-3-methene-1,6-octadiene (123-35-3) + β-naphthol (135-19-3) → 3',3'-dimethyl-1,2-dihydrospiro[benzo[f]chromene-3,1'-cyclohexane] (1039111-86-8)

Conditions	Yield
With [2,2]bipyridinyl; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 50℃; for 18h;	93%

Upstream product

• 126-91-0 linalool 
• 18172-67-3 beta-pinene 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 71092-51-8 (2-methylene-3-butenyl)-trimethyltin 
• 870-63-3 prenyl bromide 
• 2565-83-5 geraniol methyl ether 
• 141-12-8 neryl acetate 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 115-95-7 linalool acetate 
• 4075-28-9 2-chloromethyl-1,3-butadiene 
• 35189-96-9 3-methyl-2-butenylmagnesium chloride 
• 125061-34-9 4,4,4-Trifluoro-3-oxo-butyric acid (E)-3,7-dimethyl-octa-2,6-dienyl ester 
• 78-79-5 isoprene 
• 177698-19-0 Beta-pinene 

Downstream Products

• 107821-52-3 4-(4-methyl-pent-3-enyl)-cyclohex-4-ene-1,2-dicarboxylic acid 
• 29811-04-9 4-(4-methyl-3-pentenyl)-4-cyclohexene-1,2-dicarboxylic acid anhydride 
• 29811-04-9 (+/-)-4-(4-methyl-pent-3-enyl)-cyclohex-4-ene-1r,2c-dicarboxylic acid-anhydride 
• 29414-55-9 6,7-epoxymyrcene 
• 84123-50-2 1,2;5,6-diepoxy-6-methyl-2-vinyl-heptane 
• 59742-20-0 6-methyl-4-(4'-methyl-3'-pentenyl)-3-cyclohexenecarbaldehyde 
• 52475-86-2 4-methyl-1-(4-methyl-3-pentenyl)-1-cyclohexene-4-carbaldehyde 
• 101281-30-5 4-(4-methyl-pent-3-enyl)-cyclohex-4-ene-1,1,2,2-tetracarbonitrile 
• 53311-89-0 1(4-methyl-3-pentenyl)-4-carbmethoxy-cyclohex-1-ene 
• 21280-30-8 methyl ester of 1-methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carboxylic acid 
• 37677-14-8 4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carboxaldehyde 
• 52475-89-5 3-(4-methyl-3-pentenyl)-3-cyclohexene-1-carboxaldehyde 
• 73301-20-9 1-(4-methyl-3-pentenyl)cyclohexene 
• 13066-51-8 γ-geraniol 

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Relevant articles and documents

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Molybdenum- and tungsten-catalyzed allylation of aromatic compounds with allylic esters and alcohols

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.

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Selective Synthesis of 1,3-Dienic Terpenes in a β-Form through Regioselective 1,4-Elimination of Allylic Ethers

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

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.

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Thermal behavior of pinan-2-ol and linalool

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.

Preparation method of myrcene

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

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.