13466-78-9

Basic information

• Product Name: 3-CARENE
• Synonyms: 3-Carene, stabilized, 90%;δ-3-carene,3,7,7-trimethylbicyclohept-3-ene;CARENE, Delta-3-(SG);DELTA-CARENE;D-CARENE;CAREN-(3), ROH;3-CARVENE;3-CARENE WITH GC
• CAS NO: 13466-78-9
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23
• EINECS: 236-719-3
• Product Categories: Bicyclic Monoterpenes;Biochemistry;Terpenes;Miscellaneous
• Mol File: 13466-78-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 25°C
• Boiling Point: 168-169 °C705 mm Hg(lit.)
• Flash Point: 115 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 0.857 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.86mmHg at 25°C
• Refractive Index: n20/D 1.474(lit.)
• Storage Temp.: Flammables area
• Stability: Stable. Flammable. Incompatible with strong oxidizing agents.
• Merck: 1836
• CAS DataBase Reference: 3-CARENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CARENE(13466-78-9)
• EPA Substance Registry System: 3-CARENE(13466-78-9)

Safety Data

• Hazard Codes: Xi,N,Xn
• Statements: 10-43-50/53-65-38-52/53
• Safety Statements: 16-26-36/37-60-61-62-37-24
• RIDADR: UN 2319 3/PG 3
• WGK Germany: 2
• RTECS: FH8400000
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 13466-78-9(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 13466-78-9 differently. You can refer to the following data:
1. Hydroperoxides of Δ-3-carene are allergens contained in turpentine. Occupational exposure occurs in painters, varnishers, or in ceramic decoration. The percentage of Δ-3-Carene is higher in Indonesian turpentine than in Portugese.
2. (±)-3-Carene is a bicyclic monoterpene found in a variety of plants, including Cannabis. It decreases phagocytosis by rat alveolar macrophages when used at a concentration of 0.5 μM and decreases their viability at a concentration of 5 μM. (±)-3-Carene increases the expression and activity of alkaline phosphatase in mouse osteoblastic MC3T3-E1 subclone 4 cells, indicating induction of osteoblastic differentiation. It also induces calcium formation and increases the expression of osteopontin and type I collagen, which are related to osteoblast mineralization. (±)-3-Carene induces bronchoconstriction in isolated guinea pig lungs when exposed at an air concentration of 3,000 mg/m3.

Chemical Properties

Different sources of media describe the Chemical Properties of 13466-78-9 differently. You can refer to the following data:
1. Clear, colorless liquid. Stable to approx- imately 250C, resinifies with oxygen. Insoluble in water; miscible with organic solutions. Com- bustible.
2. 3-Carene has a sweet, pungent turpentine-like taste.

Occurrence

Reported present in basil oil, bell pepper, bilberry, black currant berry juice and buds, fennel oil, grapefruit juice, kumquat peel oil, lemon peel oil, lime peel oil (cold pressed and distilled), lovage seed, mandarin peel oil, orange juice, orange peel oil, orange (bitter) peel oil, tangerine peel oil and other natural products.

Uses

Solvent, intermediate. 3-Carene is a mutagenic compound that may be found in the fumes of heating freshly cut spruce and birch chips. 3-Carene is also found i many esential oils and it inhibits acetylcholinesterase activity.

Definition

A terpene hydrocarbon with both a 6-member and 3-member ring.

Preparation

Extracted from the pine tree oil.

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 5255, 1984 DOI: 10.1016/S0040-4039(01)81577-X

General Description

Colorless liquid with a sweet, turpentine-like odor. Floats on water.

Reactivity Profile

3-CARENE may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas. In the presence of various catalysts (such as acids) or initiators, may undergo exothermic addition polymerization reactions. Will attack some forms of plastics [USCG, 1999].

Health Hazard

Inhalation causes headache, confusion, respiratory distress. Ingestion irritates entire digestive system and may injure kidneys; if liquid enters lungs, it causes severe pneumonitis. Contact with eyes or skin causes irritation.

Contact allergens

Hydroperoxides of D-3-carene are allergens contained in turpentine. Occupational exposure occurs in painters, varnishers, or ceramic decoration. The percentage of D-3-carene is higher in Indonesian than in Portuguese turpentine.

InChI:InChI=1/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9+/m0/s1

Synthetic route

3,7,7-trimethyl-cyclohepta-1,3,5-triene (3479-89-8) → 1,1,4-trimethylcycloheptane (2158-55-6) + 2-carene (554-61-0) + 1,5,5-trimethylcycloheptene (7348-54-1) + 1,4,4-trimethylcycloheptene (4755-36-6) + carane (554-59-6) + 3-carene (13466-78-9)

Conditions	Yield
With hydrogen; platinum In hexane at 20 - 22℃; Product distribution; various amounts of hydrogen;	A 59% B 0.7% C 27.1% D 9.4% E 1.8% F 1.4%

2-carene (554-61-0) → 1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) + 4-methylisopropylbenzene (99-87-6) + isoterpinolene (586-63-0) + 3-carene (13466-78-9)

Conditions	Yield
thionin-supported zeolite Na-Y In hexane at 20℃; for 0.5h; Product distribution;	A 25% B 18% C 40% D 10%

3,7,7-trimethyl-cyclohepta-1,3,5-triene (3479-89-8) → 1,1,4-trimethylcycloheptane (2158-55-6) + 1,5,5-trimethylcycloheptene (7348-54-1) + 1,4,4-trimethylcycloheptene (4755-36-6) + 3-carene (13466-78-9)

Conditions	Yield
With hydrogen; platinum In hexane at 20 - 22℃; Yield given. Further byproducts given;
With hydrogen; platinum In hexane at 20 - 22℃; Yield given. Further byproducts given. Title compound not separated from byproducts;

4-hydroxymethyl-2-carene (15103-32-9) → 2-carene (554-61-0) + 3,4,7,7-tetramethyl-1,3,5-cycloheptatriene (100102-73-6) + 4-methyl-3(10),4-caradiene (103200-82-4, 106007-94-7) + 3-carene (13466-78-9)

Conditions	Yield
With potassium hydroxide at 250℃; Product distribution;	A 2.6 % Chromat. B 28.6 % Chromat. C 11.9 % Chromat. D 3.5 % Chromat.
With potassium hydroxide at 250℃;	A 2.6 % Chromat. B 28.6 % Chromat. C 11.9 % Chromat. D 3.5 % Chromat.

α-3,4-Epoxycarane (936-91-4, 936-92-5, 2225-98-1, 21218-11-1, 35671-18-2) → 3-caren-10-ol (2517-19-3) + 3,7,7-trimethyl-cyclohepta-1,3,5-triene (3479-89-8) + cara-3(10),4-diene (86361-47-9, 104048-19-3) + 3-carene (13466-78-9)

Conditions	Yield
rhenium(VII) oxide on aluminum oxide at 150℃; for 1h; Product distribution; in sealed tube, other catalysts and reaction time tested;	A 6.2 % Chromat. B 8.8 % Chromat. C 6.0 % Chromat. D 6.2 % Chromat.

3-carene (13466-78-9) → 3,4-epoxycarane (2225-98-1)

Conditions	Yield
With disodium hydrogenphosphate; 1,1,1,3',3',3'-hexafluoro-propanol; dihydrogen peroxide at 20℃; for 21h;	98%
With 1-methyl-1H-imidazole; 3-Methylpyrazole; dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane at 10℃; for 4h;	94%
With sodium dihydrogenphosphate; phosphoric acid; dihydrogen peroxide; methyl tri-n-octyl ammonium hydrogen sulfate; sodium tungstate; sodium sulfate In toluene at 70℃; for 4h;	88%

C6H4N2O4S3 (62925-73-9) + 3-carene (13466-78-9) → C16H20N2O4S3 (131843-17-9)

Conditions	Yield
In diethyl ether for 5h; Ambient temperature;	92%

3-carene (13466-78-9) → carane (554-59-6)

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 12h; Reagent/catalyst;	90%
With hydrogen; platinum In ethanol

1-phenyl-5-tetrazolyl sulfenyl chlorides (53724-68-8) + 3-carene (13466-78-9) → 3-chloro-4-(1-phenyltetrazolylthio)carane

Conditions	Yield
In 1,2-dichloro-ethane at -20 - 20℃; for 3h;	88.2%

(trifluoromethyl)trimethylsilane (81290-20-2) + 3-carene (13466-78-9) → 8,8-difluoro-1,4,4-trimethyltricyclo[5.1.0.03,5]octane

Conditions	Yield
With sodium iodide In tetrahydrofuran at 120℃; under 6000.6 Torr; for 0.166667h; Inert atmosphere; Flow reactor;	88%

3-carene (13466-78-9) → (1R,3S)-1-[3-(2-hydroxyethyl)-2,2-dimethylcyclopropyl]2-propanone

Conditions	Yield
Stage #1: 3-carene With oxygen; ozone; acetic acid In dichloromethane at -4 - -2℃; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 3h;	85%

3-carene (13466-78-9) → (3S,4S)-3,4-Dichloro-3,7,7-trimethyl-bicyclo[4.1.0]heptane

Conditions	Yield
With chloro-trimethyl-silane; tetradecyltrimethylammonium permanganate In dichloromethane at 0 - 3℃; for 1.5h;	84%

3-carene (13466-78-9) → Δ3-carene bromohydrin

Conditions	Yield
With N-Bromosuccinimide In water; acetone at 10℃;	84%

3-carene (13466-78-9) → α-3,4-Epoxycarane (936-91-4, 936-92-5, 2225-98-1, 21218-11-1, 35671-18-2)

Conditions	Yield
With diphenylphosphinic anhydride; dihydrogen peroxide; potassium carbonate In tetrahydrofuran at -5℃; for 20h;	80%
With sodium hydroxide; dihydrogen peroxide; N-tosylimidazole In methanol for 3h;	56%

3-carene (13466-78-9) + phenol (108-95-2) → 10-isopropyl-1-methyl-2-oxatricyclo[7.3.1.0.3,8]trideca-3(8),4,6-triene

Conditions	Yield
With aluminium(III) phenoxide at 150 - 160℃;	80%

methanol (67-56-1) + 3-carene (13466-78-9) → 3-methoxy-4,7,7-trimethyl-bicyclo[4.1.0]heptane + 3-methoxy-3,7,7-trimethyl-bicyclo[4.1.0]heptane

Conditions	Yield
Stage #1: methanol; 3-carene With mercury(II) diacetate at 0℃; Stage #2: With sodium In methanol at 0℃;	A n/a B 80%

3-carene (13466-78-9) → 4,7,7-trimethylbicyclo[4.1.0]heptan-3-one (13124-69-1)

Conditions	Yield
Stage #1: 3-carene With Acetoxyboran In tetrahydrofuran at 20℃; for 16h; Stage #2: With pyridinium chlorochromate In dichloromethane for 1h; Heating;	79%

3-carene (13466-78-9) → 1,1,4-trimethylcycloheptane (2158-55-6) + cis-1-isopropyl-4-methyl-cyclohexane (6069-98-3) + trans-m-menthane (6070-00-4, 6070-01-5, 13837-66-6, 13837-67-7, 16580-24-8, 17066-65-8, 17066-66-9) + cis-m-menthane (6070-00-4, 6070-01-5, 13837-66-6, 13837-67-7, 16580-24-8, 17066-65-8, 17066-66-9)

Conditions	Yield
With hydrogen; Cu + 6percent LiOH on aluminum γ-oxide at 260℃; under 11400 Torr; Further byproducts given. Yields of byproduct given;	A 78% B n/a C n/a D n/a

3-carene (13466-78-9) + 1,2-dibromomethane (74-95-3) → 1,4,4-trimethyltricyclo<5.1.0.03,5>octane (35266-89-8)

Conditions	Yield
With acetyl chloride; copper(l) chloride; zinc In diethyl ether Heating;	76%

3-carene (13466-78-9) → cis-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol

Conditions	Yield
With potassium hydroxide; tetradecyltrimethylammonium permanganate In dichloromethane; tert-butyl alcohol at 30℃; for 1h;	71%

3-carene (13466-78-9) → 4-hydroxy-3-hydroperoxycarene + carane-3,4-diol (57526-47-3)

Conditions	Yield
With dihydrogen peroxide; magnesium sulfate; tert-butyl alcohol; tungsten boride In water at 25 - 40℃; for 25.5h;	A 70.4% B 21.7%

3-carene (13466-78-9) → 1-((1R,3S,5S)-6,6-dimethylbicyclo[3.1.0]hexan-3-yl)ethan-1-one (32543-81-0)

Conditions	Yield
With thallium(III) nitrate In methanol Ambient temperature;	70%
With thallium(III) nitrate In methanol Ambient temperature;	70%

3-carene (13466-78-9) → carane-3,4-diol (57526-47-3)

Conditions	Yield
With dihydrogen peroxide; tert-butyl alcohol; tungsten In water at 25℃; for 25.5h;	70%
With formic acid; dihydrogen peroxide hydroxylation;
With osmium(VIII) oxide In dichloromethane
Multi-step reaction with 2 steps 1: MCPA / H2O 2: H2SO4; water View Scheme

3-carene (13466-78-9) → 3,4-epoxycarane (2225-98-1) + 2,2-dimethyl cyclohepta-3,5-diene-1-one

Conditions	Yield
With cobalt dichloride; oxygen; 2-ethoxycarbonyl-1-cyclopentanone In acetonitrile for 40h;	A n/a B 68%
With cobalt dichloride; oxygen; isobutyraldehyde In acetonitrile	A 47% B 35%

dimethyl sulfide borane (13292-87-0) + 3-carene (13466-78-9) → B-methoxydiisocaranylborane

Conditions	Yield
In tetrahydrofuran (N2), BH3*SMe2 in THF cooled to 0°C in ice bath, carene added dropwise with stirring, maintained at 0°C for 20 h with stirring; crystals washed with ice-cold Et2O, solid taken up in THF, MeOH added dropwise at 0°C, mixture stirred at 0°C for 2 h, slowly warmed to room temp., stirred at 25°C for 1 h, solvent removed under vac.;	68%

3-carene (13466-78-9) → (+/-)-Car-3-ene-2,5-dione (67670-71-7, 67670-72-8, 6617-34-1)

Conditions	Yield
With tert.-butylhydroperoxide; oxygen In acetonitrile at 70℃; for 2h; Green chemistry;	61.2%
With tert.-butylhydroperoxide; bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; water at 20℃; for 24h; Sealed tube; regioselective reaction;	60%
With tert.-butylhydroperoxide; sodium hydrogencarbonate; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at -30 - 20℃; for 6h;	35%

3-carene (13466-78-9) → 2-(2,2-dimethyl-3-(2-oxopropyl)cyclopropyl)acetic acid (99265-61-9)

Conditions	Yield
With sodium periodate; ruthenium(III) trichloride hydrate In water; tert-butyl alcohol at 35 - 55℃; for 3.5h;	59%
With sodium periodate; rhodium(III) chloride hydrate In water; tert-butyl alcohol at 35 - 55℃; for 3.5h; Inert atmosphere;	59%
With sodium periodate; rhodium(III) chloride hydrate In water; tert-butyl alcohol at 45 - 55℃; for 3.5h; Temperature;

palladium dichloride + 3-carene (13466-78-9) → Pd2Cl2(C10H15)2 (89606-45-1)

Conditions	Yield
With potassium acetate In acetic acid equimolar amts., 55-60°C, 4 h;	50%

3-carene (13466-78-9) → 2,2-dimethyl cyclohepta-3,5-diene-1-one

Conditions	Yield
With oxygen; isobutyraldehyde; (MeO2CCH(Bn)N=CH(C6H4O)-o)2Co In acetonitrile at 25℃;	48%

3-carene (13466-78-9) → 3-acetyl-6,6-dimethylbicyclo<3.1.0>hexane (1856-74-2) + 2α-Bromo-3β-hydroxy-3,7,7-trimethylbicyclo<4.1.0>heptane (94450-61-0)

Conditions	Yield
With N-Bromosuccinimide; N,N-dimethyl-formamide at 70℃; for 10h;	A 25% B 40%

3-carene (13466-78-9) → C10H16O2

Conditions	Yield
With potassium permanganate; water In acetone at 5℃; for 12h; Temperature;	40%

3-carene (13466-78-9) → 1,1,4-trimethylcycloheptane (2158-55-6)

Conditions	Yield
With hydrogen; platinum on activated charcoal at 70℃; Product distribution; other temperature; other catalyst;	37%

acetic acid (64-19-7) + 3-carene (13466-78-9) → C12H18O2 (13837-89-3)

Conditions	Yield
With 2-[(phenylmethyl) thio]-5-methyl-1,3,4-thiadiazole; palladium diacetate; triethylamine; p-benzoquinone at 40℃; Inert atmosphere; Green chemistry; regioselective reaction;	32%

Upstream product

• 917-54-4 methyllithium 
• 94806-25-4 (E)-4-(Tri-n-butylstannyl)-3-buten-2-one 
• 78-79-5 isoprene 
• 554-61-0 2-carene 
• 80-56-8 Pinene 
• 936-91-4 α-3,4-Epoxycarane 
• 15103-32-9 4-hydroxymethyl-2-carene 
• 3479-89-8 3,7,7-trimethyl-cyclohepta-1,3,5-triene 
• 116872-39-0 (+/-)-10-phenylsulfonylcar-3-ene 

Downstream Products

• 131843-17-9 C₁₆H₂₀N₂O₄S₃ 
• 1195-32-0 1-methyl-4-isopropenylbenzene 
• 535-77-3 m-cymene 
• 99-87-6 4-methylisopropylbenzene 
• 1124-20-5 2-(3-methylphenyl)propene 
• 7348-54-1 1,5,5-trimethylcycloheptene 
• 4755-36-6 1,4,4-trimethylcycloheptene 
• 554-61-0 2-carene 
• 3479-89-8 3,7,7-trimethyl-cyclohepta-1,3,5-triene 
• 554-59-6 trans-Carane 
• 88070-28-4 3,6,6-trimethylcycloheptene 
• 1197-01-9 p-cymene-8-ol 
• 81800-50-2 3,7,7-trimethylbicyclo(4,1,0)hept-3-en-5-one 
• 98-55-5 terpineol 

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Detection of 3-CARENE (cas 13466-78-9) in mango using a quartz crystal microbalance sensor08/09/2019

The exacting technology of piezoelectric aroma sensor has engendered a great hope for determining the ripening aroma of mango (Mangifera indica L.). 3-Carene is one of the most important ripeness indicating aromas of mango. Detection of 3-Carene content in mango is very important because fruit a...detailed

Measurement and correlation of vapor–liquid equilibrium data for binary and ternary systems composed of (−)-β-caryophyllene, p-cymene and 3-CARENE (cas 13466-78-9) at 101.33 kPa08/07/2019

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Catalytic isomerization of α-pinene and 3-CARENE (cas 13466-78-9) in the presence of modified layered aluminosilicates08/06/2019

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