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138-86-3

Basic Information
CAS No.: 138-86-3
Name: Cinene
Article Data: 400
Molecular Structure:
Molecular Structure of 138-86-3 (Cinene)
Formula: C10H16
Molecular Weight: 136.237
Synonyms: (+-)-Dipentene;(+-)-Linonene;Limonene;(+-)-alpha-Limonene;1,8-p-Menthadiene;1-Methyl-4-(1-methylethenyl)cyclohexene;1-Methyl-4-isopropenyl-1-cyclohexene;1-Methyl-p-isopropenyl-1-cyclohexene;4-Isopropenyl-1-methyl-1-cyclohexene;AI3-00739;
EINECS: 205-341-0
Density: 0.834 g/cm3
Melting Point: -84 - -104 °C
Boiling Point: 175.44 °C at 760 mmHg
Flash Point: 42.778 °C
Solubility: water: <1 g/100mL
Appearance: colourless or light yellow liquid
Hazard Symbols: IrritantXi,DangerousN
Risk Codes: 10-38-43-50/53
Safety: 24-37-60-61
Transport Information: UN 2052 3/PG 3
PSA: 0.00000
LogP: 3.30890
Synthetic route
18172-67-3

(−)-β-pinene

7785-26-4

2,6,6-trimethylbicyclo[3.1.1]hept-2-ene

B

138-86-3

limonene.

Conditions
ConditionsYield
In liquid sulphur dioxide Ambient temperature;A 97%
B 3%
In liquid sulphur dioxide Rate constant; Mechanism; Kinetics; Ambient temperature;A 97%
B 3%
1195-92-2

Limonene oxide

138-86-3

limonene.

Conditions
ConditionsYield
With lithium; biphenyl In 1,2-dimethoxyethane for 4h; Heating; other solvents, other temperatures, other reaction times, other catalysts;96%
With lithium In tetrahydrofuran for 82h; Heating;86%
With isopropyl alcohol In toluene at 110℃; for 24h; Inert atmosphere; chemoselective reaction;68 %Chromat.
Conditions
ConditionsYield
With H2SiEt2; tris(pentafluorophenyl)borate In dichloromethane86%
With boron trifluoride diethyl etherate; sodium cyanoborohydride In tetrahydrofuran for 3h; Ambient temperature;50%
79433-08-2

(2Z,6E)-3,7-dimethyl-8-trimethylsilyl-2,6-octadien-1-ol

138-86-3

limonene.

Conditions
ConditionsYield
With titanium tetrachloride; N-methylaniline In dichloromethane at -23℃; for 1h;77%
79433-10-6

(2Z,6E)-3,7-dimethyl-8-tributylstannyl-2,6-octadien-1-ol

138-86-3

limonene.

Conditions
ConditionsYield
With titanium tetrachloride; N-methylaniline In dichloromethane at -23℃; for 2h;73%
536-59-4

perillol

138-86-3

limonene.

Conditions
ConditionsYield
With methanol; toluene-4-sulfonic acid at 25℃; for 18h; Inert atmosphere; Sealed tube; UV-irradiation;73%
limonene sulphide

limonene sulphide

138-86-3

limonene.

Conditions
ConditionsYield
With biphenyl; lithium In 1,2-dimethoxyethane for 16h; Heating;71%
177698-19-0

Beta-pinene

B

1195-32-0

1-methyl-4-isopropenylbenzene

C

79-92-5

camphene

D

C20H32

E

138-86-3

limonene.

Conditions
ConditionsYield
With hydrogen at 140℃; for 4h; Temperature; Reagent/catalyst;A n/a
B n/a
C n/a
D 65.6%
E n/a
106-24-1

Geraniol

A

3338-55-4

(Z)-ocimene

B

3779-61-1

trans ocimene

C

138-86-3

limonene.

Conditions
ConditionsYield
With sesquiterpene synthases Cop4 from Coprinus cinereus In terpene synthase buffer at 25℃; for 18h; Enzymatic reaction;A 61%
B 9.1%
C 23.7%
79433-11-7

Acetic acid (2Z,6E)-3,7-dimethyl-8-tributylstannanyl-octa-2,6-dienyl ester

138-86-3

limonene.

Conditions
ConditionsYield
With methylaluminium bis(trifluoroacetate) In hexane at 25℃; for 21h;51%
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  • Casno:

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    Dipentene

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  • Cyclohexene,1-methyl-4-(1-methylethenyl)-

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Reported in EPA TSCA Inventory.

Specification

The d-limonene , with the CAS register number 138-86-3, is also known to us as (S)-(-)-4-ISOPROPENYL-1-METHYL-1-CYCLOHEXENE;(±)-1,8-p-menthadiene,(±)-limonene;(±)-limonene(dipentene);1,8(9)-p-Menthadiene;1,8-p-Menthadiene;1-methyl-4-(1-methylethenyl)-cyclohexen;1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene;1-Methyl-4-isopropenyl-1-cyclohexene .

The characteristics of this kind of chemical are as followings: (1)Index of Refraction:  1.467  ; (2)Molar Refractivity:  45.35 cm ; (3)Molar Volume:  163.2 cm3  ; (4)Polarizability:  17.98 ×10-24 cm3  ; (5)Surface Tension:  25.8 dyne/cm  ; (6)Density:  0.834 g/cm ; (7)Flash Point:  42.8 °C  ; (8)Enthalpy of Vaporization:  39.49 kJ/mol  ; (9)Boiling Point:  175.4 °C at 760 mmHg  ; (10)Vapour Pressure:  1.54 mmHg at 25°C .

It is a kind of transparent flammable liquid with good smelling. And it is stable and incompatible with strong oxidizing agents. Besides, it is insoluble with water but soluble in ethanol. Its categories are including biochemistry;monocyclic monoterpenes;terpenes;alphabetical listings;flavors and fragrances;i-l . As for its usage, it could be used in composing rubber and be used as the raw material of spice and also could be solvent.

Being the irritant chemicals, it may cause inflammation to the skin or other mucous membranes and may cause sensitization by skin contact, so you need to be very cautious while using it. Wear suitable gloves and avoid contact with skin. Besides, it is also dangerous for the environment, for it may present an immediate or delayed danger to one or more components of the environment. It is very toxic to aquatic organisms, and may cause long-term adverse effects in the aquatic environment. So while dealing with it, this material and its container must be disposed of as hazardous waste. And then avoid release to the environment and refer to special instructions/safety data sheet if necessary. Except all these, it is a very dangerous as it could mix with air to make explosion, so store it seperately with other flammable chemicals.

In addition, you could refer to the following datas to get the molecular structure:
SMILES:C=C(\[C@H]1C/C=C(/C)CC1)C
InChI:InChI=1/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m0/s1
InChIKey:XMGQYMWWDOXHJM-JTQLQIEIBU 

Below are the toxicity information of d-limonene :

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LDLo unreported 4600mg/kg (4600mg/kg)   Reviews of Environmental Contamination and Toxicology. Vol. 113, Pg. 47, 1990.
 
mouse LD50 intravenous 1010uL/kg (1.01mL/kg)   Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 24, Pg. 700, 1989.
mouse LD50 oral 5550uL/kg (5.55mL/kg)   Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 24, Pg. 700, 1989.
rat LD50 oral 5300mg/kg (5300mg/kg)   Food and Cosmetics Toxicology. Vol. 12, Pg. 703, 1974.