13877-91-3

Basic information

• Product Name: OCIMENE
• Synonyms: FEMA 3539;3,7-DIMETHYL-1,3,6-OCTATRIENE;3,6-Octatriene,3,7-dimethyl-1;6-octatriene,3,7-dimethyl-3;ocimene,mixtureofisomers;p-Ocimene;OCIMENE;3,7-dimethylocta-1,3,6-triene
• CAS NO: 13877-91-3
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23
• EINECS: 237-641-2
• Mol File: 13877-91-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: -27.17°C (estimate)
• Boiling Point: 65-66 °C/13 mmHg
• Flash Point: 38 °C
• Appearance: colourless clear liquid
• Density: 0.818 g/mL at 20 °C(lit.)
• Vapor Pressure: 2.207hPa at 24℃
• Refractive Index: n20/D 1.485
• Storage Temp.: 2-8°C
• Water Solubility: 14.5mg/L at 24℃
• BRN: 1736172
• CAS DataBase Reference: OCIMENE(CAS DataBase Reference)
• NIST Chemistry Reference: OCIMENE(13877-91-3)
• EPA Substance Registry System: OCIMENE(13877-91-3)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: UN2319 3/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 13877-91-3(Hazardous Substances Data)

Usage

Description

β-Ocimene is a monoterpene that has been found in a variety of plants and is a volatile compound involved in plant-plant signaling and plant defense against pests. It is emitted by tea (C. sinensis) plants in response to a jasmonic acid combined with mechanical damage (JAMD) model of herbivore attack. β-Ocimene reduces the number of winged aphids (M. persicae) that settle on Chinese cabbage and the feeding time and number of nymphs produced by aphids on leaves. The aphid endoparasitoid A. gifuensis demonstrates a preference for β-ocimene-treated Chinese cabbage over control plants in a wind tube two-choice test. β-Ocimene (100-1,000 ppm) also has antioxidant activity in a thiobarbituric acid reactive substances (TBARS) assay.

Chemical Properties

3,7-Dimethyl-1,3,6-octatrine has a warm herbaceous odor.

Occurrence

Reported found in black currants, currant leaves, mentha pulegium oil, origanum oil, passion fruit, citrus peel oils, guava, strawberry jam, cinnamon bark, Thymus vulgaris, hop oil, tea, soybean, parsnips, tarragon, origanum, Ocimum basilicum, curcuma, ouzo and pimento berry

Taste threshold values

Taste characteristics at 40 ppm: green, tropical, woody with floral and vegetable nuances.

Flammability and Explosibility

Flammable

Synthesis

One-step synthesis of trans-beta-ocimene

InChI:InChI=1/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7-8H,1,6H2,2-4H3/b10-8+

Synthetic route

3,7-dimethylocta-1,6-dien-3-ol (78-70-6) → 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) + Terpinolene (586-62-9) + limonene. (138-86-3)

Conditions	Yield
With rhenium(VII) oxide In toluene at 100℃; for 24h;	A 32% B 22% C 43%
With sulfuric acid In toluene at 100℃; for 24h;	A 11% B 25% C 20%

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%

pyridine (110-86-1) + geranyl bromide (6138-90-5) → 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) + limonene. (138-86-3)

Conditions	Yield
at 140℃;

(+)-α-pinene (7785-70-8) → 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) + limonene. (138-86-3)

Conditions	Yield
at 54℃; unter vermindertem Druck;
at 350℃;

2,6-dimethyl-hepta-1,5-diene (6709-39-3) + bromomethanesulfonyl bromide (54730-18-6) → 7-methyl-3-methene-1,6-octadiene (123-35-3) + 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran; tert-butyl alcohol at -23 - 25℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

3,7-dimethyl-2E,6-octadien-1-yl acetate (105-87-3) → dihydromyrcene (2436-90-0) + dihydromyrcene (2492-22-0, 2609-23-6, 2792-39-4) + 7-methyl-3-methene-1,6-octadiene (123-35-3) + 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3)

Conditions	Yield
With ammonium formate; bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine In tetrahydrofuran at 65℃; for 2h; Product distribution; other catalysts, other ligands, other solvents, other time, other temp.;

linalool acetate (115-95-7) → 7-methyl-3-methene-1,6-octadiene (123-35-3) + 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3)

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; molybdenum hexacarbonyl for 1h; Heating; Yield given. Yields of byproduct given;

geranyl diphosphate (763-10-0) → 3,7-dimethylocta-1,6-dien-3-ol (78-70-6) + 7-methyl-3-methene-1,6-octadiene (123-35-3) + Nerol (106-25-2) + Geraniol (106-24-1) + 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) + terpineol (98-55-5)

Conditions	Yield
With N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid; manganese(II) In water at 40℃; Product distribution; Thermodynamic data; Kinetics; investigation of the effect of pH, stoichiometry, kind and concentration of catalyst and temperature;

3,7-dimethyl-1-(N-methyl-2-imidazolylthio)-2,6-octadiene (81678-25-3) → 3,7-dimethylocta-1,6-dien-3-ol (78-70-6) + 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) + terpineol (98-55-5)

Conditions	Yield
With hydrogenchloride at 20℃; for 5h; other alkylmercaptoazoles;

2-nerylmercapto-1-methylimidazole (81678-26-4) → 7-methyl-3-methene-1,6-octadiene (123-35-3) + 3,7-dimethyl-3-methoxy-1,6-octadiene (60763-44-2) + 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) + (2Z)-1-methoxy-3,7-dimethylocta-2,6-diene (2565-83-5) + 4-(2-methoxypropan-2-yl)-1-methylcyclohex-1-ene (14576-08-0)

Conditions	Yield
With hydrogenchloride for 5h; Product distribution; Irradiation; other alkylmercaptoazoles, var solvents and temperatures;

(E)-1-Bromomethanesulfonyl-2,6-dimethyl-hepta-1,5-diene → 7-methyl-3-methene-1,6-octadiene (123-35-3) + 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran; tert-butyl alcohol Yield given. Yields of byproduct given;

3,7-dimethylocta-1,6-dien-3-ol (78-70-6) + acetic anhydride (108-24-7) → 7-methyl-3-methene-1,6-octadiene (123-35-3) + 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) + limonene. (138-86-3) + 1-acetoxy-3,7-dimethyl-octa-2t,6-diene

sulfuric acid (7664-93-9) + alloocimene (3016-19-1) → 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3)

(±)-linalyl diphosphate (16789-26-7) → 3,7-dimethylocta-1,6-dien-3-ol (78-70-6) + 7-methyl-3-methene-1,6-octadiene (123-35-3) + Nerol (106-25-2) + Geraniol (106-24-1) + 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) + terpineol (98-55-5) + limonene

Conditions	Yield
With water at 30℃; Rate constant; Product distribution; with/without complexing agent (Mg(2+), Mn(2+)), pH 7.0;

linalyl monophosphate (16751-03-4) → 3,7-dimethylocta-1,6-dien-3-ol (78-70-6) + 7-methyl-3-methene-1,6-octadiene (123-35-3) + Nerol (106-25-2) + Geraniol (106-24-1) + 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) + terpineol (98-55-5) + limonene

Conditions	Yield
With water at 40℃; Rate constant; Product distribution; with/without complexing agent (Mg(2+), Mn(2+)), pH 7.0;

2,6-dimethyl-hepta-1,5-diene (6709-39-3) → 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: CH2Cl2 / 0 °C 2: Et3N / CH2Cl2 3: KO-t-Bu / tetrahydrofuran; 2-methyl-propan-2-ol View Scheme

6-Bromo-7-bromomethanesulfonyl-2,6-dimethyl-hept-2-ene → 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 2: KO-t-Bu / tetrahydrofuran; 2-methyl-propan-2-ol View Scheme

Geraniol (106-24-1) → 3,7-dimethylocta-1,6-dien-3-ol (78-70-6) + 7-methyl-3-methene-1,6-octadiene (123-35-3) + 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) + beta-phellandrene (555-10-2) + (R)-5-isopropyl-2-methylcyclohexa-1,3-diene (4221-98-1) + 3,7-dimethyl-1,3,7-octatriene

Conditions	Yield
With boron pentasil zeolite at 220℃; under 60.006 Torr; for 2h; Gas phase;

diazomethane (186581-53-3, 908094-01-9) + 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) → 2-cyclopropyl-6-methyl-2,5-heptadiene

Conditions	Yield
Stage #1: 3,7-Dimethyl-octa-1,3,6-trien With benzophenone In 1,4-dioxane at 20℃; Stage #2: diazomethane In 1,4-dioxane at 15℃; for 2h; Solvent; Temperature;	96.92%

3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) + 1,1-dibromomethane (74-95-3) → 2-cyclopropyl-6-methyl-2,5-heptadiene

Conditions	Yield
With [i-PrPDI]CoBr2; zinc In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; regioselective reaction;	81%

3,4-dihydroxybenzoic acid methyl ester (2150-43-8) + 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) → C18H22O4 (1529815-47-1)

Conditions	Yield
With silver(l) oxide In diethyl ether; toluene at 0 - 20℃; for 23h; Diels-Alder Cycloaddition;	80.5%

3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) + 2,5-dihydroxybenzoic acid. (490-79-9) → C16H20O2 (1529815-53-9)

Conditions	Yield
With [bis(acetoxy)iodo]benzene In di-isopropyl ether; acetonitrile at 0℃; for 1h; Diels-Alder Cycloaddition;	64.28%

3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) + C18H16O5 → (+)-Panduratin A + (+)-panduratin A

Conditions

Yield

Stage #1: C18H16O5 With borane-THF; acetic acid; (2S)-(-)-3,3'-diphenyl-(2,2'-binaphthalene)-1,1'-diol In tetrahydrofuran at 20℃; for 1h; Diels-Alder Cycloaddition; Molecular sieve; Inert atmosphere; Stage #2: 3,7-Dimethyl-octa-1,3,6-trien In tetrahydrofuran at 20℃; for 68h; Diels-Alder Cycloaddition; Molecular sieve; Inert atmosphere; Stage #3: With sodium hydrogencarbonate In methanol at 20℃; for 8h; Inert atmosphere; enantioselective reaction;

A 58% B n/a

3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) → C10H16O2 (1262225-79-5) + (E)-2,2-dimethyl-3-(3-methylpenta-2,4-dienyl)oxirane (28977-57-3)

Conditions	Yield
Stage #1: 3,7-Dimethyl-octa-1,3,6-trien With N-Bromosuccinimide; dimethyl sulfoxide at 10℃; for 0.5h; Inert atmosphere; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 0℃; for 0.5h; Inert atmosphere;	A 47% B 56%

1-indoline (496-15-1) + 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) → (E)-1-(3,7-dimethylocta-3,6-dien-1-yl)indoline

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; MANDELIC ACID In 1,2-dichloro-ethane at 80℃; for 15h; Glovebox; regioselective reaction;	51%

3,4-Dihydroxybenzoic acid (99-50-3) + 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) → C16H20O2 (1529815-52-8)

Conditions	Yield
With [bis(acetoxy)iodo]benzene In di-isopropyl ether; acetonitrile at 0℃; for 1h; Diels-Alder Cycloaddition;	50.84%

3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) + dilauryl peroxide (105-74-8) → C33H62O2

Conditions	Yield
With copper(I) thiophene-2-carboxylate In 1,4-dioxane at 70℃; for 4h; Schlenk technique; Inert atmosphere; regioselective reaction;	43%

3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) → (Z)-2,2-dimethyl-3-(3-methylpenta-2,4-dienyl)oxirane + 2-methyl-3-(3-methyl-but-2-enyl)-2-vinyl-oxirane + (E)-2,2-dimethyl-3-(3-methylpenta-2,4-dienyl)oxirane (28977-57-3)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 1h; Epoxidation; Title compound not separated from byproducts;	A n/a B 20% C n/a

benzimidazole (271-44-3) + 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) → C17H22N2

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); triethyl borane; 1,2-bis[di(t-butyl)phosphinomethyl]benzene In isopropyl alcohol at 80℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction;	10%

3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) → 2,6-dimethyloctane (2051-30-1)

Conditions	Yield
With hydrogen; nickel at 130℃;

3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) → dihydromyrcene (2492-22-0, 2609-23-6, 2792-39-4)

Conditions	Yield
With ethanol; sodium

3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) → (E,E)-2,6-dimethyl-2,4,6-octatriene (3016-19-1)

Conditions	Yield
bei laengerem Erhitzen;

3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) → alloocimene (3016-19-1)

3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) + acetyl chloride (75-36-5) → 7-acetoxy-3,7-dimethyl-octa-1,3-diene (72214-23-4)

Conditions	Yield
(i) benzene-1,4-diol, H2SO4, aq. AcOH, (ii) /BRN= 605303/, PhNMe2; Multistep reaction;

3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) + dimethyl acetylenedicarboxylate (762-42-5) → 4-Methyl-3-(3-methyl-but-2-enyl)-cyclohexa-1,4-diene-1,2-dicarboxylic acid

Conditions	Yield
(i) , (ii) KOH, MeOH; Multistep reaction;

3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) + [1,4]naphthoquinone (130-15-4) → 2-Methyl-1-(3-methyl-but-2-enyl)-1,4,4a,9a-tetrahydro-anthraquinone (111977-49-2)

Conditions	Yield
In ethanol Heating;

3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) + hexachlorocyclopentadiene (77-47-4) → (1S,4R,5S)-1,2,3,4,7,7-Hexachloro-5-((E)-1,5-dimethyl-hexa-1,4-dienyl)-bicyclo[2.2.1]hept-2-ene

Conditions	Yield
at 90℃;

3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) → 3,7-dimethylocta-1,6-dien-3-ol (78-70-6) + Nerol (106-25-2)

Conditions	Yield
With sodium hydroxide; boric acid tributyl ester; dihydrogen peroxide; magnesium 1) THF, 25 deg C --> reflux; 2) 0 - 5 deg C, THF; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

Upstream product

• 110-86-1 pyridine 
• 6138-90-5 geranyl bromide 
• 7785-70-8 (+)-α-pinene 
• 115-95-7 linalool acetate 
• 763-10-0 geranyl diphosphate 
• 81678-25-3 3,7-dimethyl-1-(N-methyl-2-imidazolylthio)-2,6-octadiene 
• 81678-26-4 2-nerylmercapto-1-methylimidazole 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 108-24-7 acetic anhydride 
• 7664-93-9 sulfuric acid 
• 3016-19-1 alloocimene 
• 16789-26-7 (±)-linalyl diphosphate 
• 16751-03-4 linalyl monophosphate 
• 106-24-1 Geraniol 

Downstream Products

• 3016-19-1 (E,E)-2,6-dimethyl-2,4,6-octatriene 
• 3016-19-1 alloocimene 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 106-25-2 Nerol 
• 69103-20-4 (Z)-myroxide 
• 28977-57-3 (E)-myroxide 
• 6874-44-8 cis-α-ocimene 
• 6874-10-8 1,3,7-octatriene, 3,7-dimethyl-, (E) 
• 1262225-79-5 C₁₀H₁₆O₂ 
• 72214-23-4 7-acetoxy-3,7-dimethyl-octa-1,3-diene 

Relevant articles and documents

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Mechanistic insights into the rhenium-catalyzed alcohol-to-olefin dehydration reaction

Rhenium-based complexes are powerful catalysts for the dehydration of various alcohols to the corresponding olefins. Here, we report on both experimental and theoretical (DFT) studies into the mechanism of the rhenium-catalyzed dehydration of alcohols to olefins in general, and the methyltrioxorhenium-catalyzed dehydration of 1-phenylethanol to styrene in particular. The experimental and theoretical studies are in good agreement, both showing the involvement of several proton transfers, and of a carbenium ion intermediate in the catalytic cycle. Ionic or concerted? Rhenium-based complexes are powerful catalysts for the dehydration of various alcohols to the corresponding olefins. Experimental and DFT studies into the mechanism of the rhenium-catalyzed dehydration of alcohols to olefins are reported. The experimental and theoretical studies are in good agreement, both showing the involvement of a carbenium ion intermediate in the catalytic cycle (see figure). Copyright

Cyclization of citronellal in a supercritical solvent in a flow reactor in the presence of Al2O3

The reactivity of citronellal under supercritical solvent conditions in a flow reactor in the presence of Al2O3 is examined. It is shown that at 160°C, the main transformation product of citronellal is isopulegol, and when the temperature is increased to 190°C, they are monoterpenes with a para-menthane framework and myrcene. Pleiades Publishing, Ltd., 2012.

Preparation of 1-Alkenes by the Palladium-Catalyzed Hydrogenolysis of Terminal Allylic Carbonates and Acetates with Formic Acid-Triethylamine

A useful method for the preparation of 1-alkenes from terminal allylic carbonates and acetates by the palladium-catalyzed reaction with formates is described.Formic acid-triethylamine is a suitable reductant.As catalyst, Pd2(dba)3CHCl3-P(n-Bu)3 gave the best result, 0.05-0.2 molpercent being sufficient (turnover 500-2000).Using this method, various 1-alkenes were prepared in good yields with high selectivity.