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(R)-(+)-Limonene

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Name

(R)-(+)-Limonene

EINECS 227-813-5
CAS No. 5989-27-5 Density 0.834 g/cm3
PSA 0.00000 LogP 3.30890
Solubility insoluble in water Melting Point -75--73 °C
Formula C10H16 Boiling Point 175.4 °C at 760 mmHg
Molecular Weight 136.237 Flash Point 42.8 °C
Transport Information UN 2052 3/PG 3 Appearance Colorless oily liquid
Safety 24-37-60-61 Risk Codes 10-38-43-50/53
Molecular Structure Molecular Structure of 5989-27-5 (D-Limonene) Hazard Symbols IrritantXi, DangerousN
Synonyms

Cyclohexene,1-methyl-4-(1-methylethenyl)-, (R)-;p-Mentha-1,8-diene, (R)-(+)- (8CI);(+)-(4R)-Limonene;(+)-(R)-Limonene;(+)-Dipentene;(+)-Limonene;(+)-p-Mentha-1,8-diene;(+)-a-Limonene;(4R)-(+)-Limonene;(4R)-1-Methyl-4-(1-methylethenyl)cyclohexene;(4R)-Limonene;D-(+)-Limonene;(R)-p-Mentha-1,8-diene;(R)-(+)-Limonene;

Article Data 46

(R)-(+)-Limonene Synthetic route

Phosphoric acid diethyl ester (R)-5-isopropenyl-2-methyl-cyclohex-1-enyl ester

5989-27-5

D-limonene

Conditions
ConditionsYield
With ammonia; lithium80%
308363-12-4

L-carveol

5989-27-5

D-limonene

Conditions
ConditionsYield
With 2-nitrobenzenesulfonyl hydrazide; triphenylphosphine; diethylazodicarboxylate In various solvent(s) -30 deg, 1 h; 23 deg C 30 min;78%
2102-58-1

(+)-trans-carveol

5989-27-5

D-limonene

Conditions
ConditionsYield
With triethylsilane; lithium perchlorate In diethyl ether for 16h; Ambient temperature;68%

1-[2-((R)-4-Methyl-cyclohex-3-enyl)-prop-2-ene-1-sulfonyl]-propan-2-one

5989-27-5

D-limonene

Conditions
ConditionsYield
With aluminum amalgam In tetrahydrofuran; water at 20℃; for 4h;58%

C16H27BO2

5989-27-5

D-limonene

Conditions
ConditionsYield
With acetic acid at 120℃;22%
7785-70-8

(+)-α-pinene

5989-27-5

D-limonene

Conditions
ConditionsYield
With fired clay at 25℃;
With fired clay; acetic anhydride; acetic acid at 10℃;
With fired clay; acetic anhydride; acetic acid at 25℃;
88-89-1

2,4,6-Trinitrophenol

71-43-2

benzene

A

5989-27-5

D-limonene

B

bornyl-picryl ether

C

79-92-5

(+)-camphene

D

138-86-3

limonene.

Conditions
ConditionsYield
at 120℃; d-α-pinene;
85-52-9

2-Benzoylbenzoic acid

7785-70-8

(+)-α-pinene

5989-27-5

D-limonene

Conditions
ConditionsYield
at 140℃;
85-52-9

2-Benzoylbenzoic acid

127-91-3

(1R,5R)-(+)-β-pinene

5989-27-5

D-limonene

Conditions
ConditionsYield
at 140℃;
86851-45-8

(R)-(+)-binaphthol mononeryl ether

A

586-62-9

Terpinolene

B

5989-27-5

D-limonene

C

5989-54-8

(-)-(S)-limonene

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; tri-tert-butylphenol; diisobutylaluminium hydride 2.) 3 h, -130 deg C, CCl3F; Yield given. Multistep reaction. Yields of byproduct given;

(R)-(+)-Limonene Specification

The (R)-(+)-Limonene, with CAS registry number of 5989-27-5 is also known as (R)-(+)-Limonene. The systematic name is (4R)-1-Methyl-4-prop-1-en-2-ylcyclohexene. It belongs to product categories of Biochemistry; Monocyclic Monoterpenes; Terpenes; Phenyls & Phenyl-Het. Its EINECS registry number is 227-813-5. In addition, the formula is C10H16 and the molecular weight is 136.23. The (R)-(+)-Limonene is a colorless oily liquid that colorless oily liquid and also may present an immediate or delayed danger to one or more components of the environment.And it is highly flammable. Insoluble in water.

Physical properties about (R)-(+)-Limonene are:
(1)ACD/LogP: 4.45; (2)#Freely Rotating Bonds: 1; (3)Index of Refraction: 1.467; (4)Molar Refractivity: 45.35 cm3; (5)Molar Volume: 163.2 cm3; (6)Surface Tension: 25.8 dyne/cm; (7)Density: 0.834 g/cm3; (8)Flash Point: 42.8 °C; (9)Enthalpy of Vaporization: 39.49 kJ/mol; (10)Boiling Point: 175.4 °C at 760 mmHg; (11)Vapour Pressure: 1.54 mmHg at 25 °C.

Preparation of (R)-(+)-Limonene:
it is prepared by reaction of (2R)-trans-p-mentha-6,8-dien-2-ol. The reaction needs reagents 3M LiClO4, Et3SiH and solvent diethyl ether with other condition of ambient temperature for 16 hours. The yield is about 68%.
Cyclohexene,1-methyl-4-(1-methylethenyl)-, (4R)- is prepared by reaction of (2R)-trans-p-mentha-6,8-dien-2-ol.

Uses of (R)-(+)-Limonene:
it is used to produce Preparation of Cyclohexene,1-methyl-4-(1-methylethenyl)-, (4R)- by reaction with phenylsilane. The reaction occurs with catalyst Cp*2YCH(TMS)2 and solvent benzene with other condition of ambient temperature for 96 hours. The yield is about 61%.Cyclohexene,1-methyl-4-(1-methylethenyl)-, (4R)- is used to produce Preparation of Cyclohexene,1-methyl-4-(1-methylethenyl)-, (4R)- by reaction with phenylsilane.

Safety information of  (R)-(+)-Limonene:
When you are using (R)-(+)-Limonene, please be cautious about it. As a chemical, it is irritating to skin, flammable and it may cause sensitisation by skin contact. Besides, (R)-(+)-Limonene is very toxic to aquatic organisms that may cause long-term adverse effects in the aquatic environment. During using it, wear suitable gloves. Avoid contact with skin and eyes and avoid release to the environment. After using it, this material and its container must be disposed of as hazardous waste.

You can still convert the following datas into molecular structure:
(1)SMILES:C=C(\[C@H]1C/C=C(/C)CC1)C;
(2)Std. InChI:InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m0/sl;
(3)Std. InChIKey:XMGQYMWWDOXHJM-JTQLQIEISA-N.

The toxicity data of (R)-(+)-Limonene is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 skin > 5gm/kg (5000mg/kg)   Food and Cosmetics Toxicology. Vol. 12, Pg. 703, 1974.
mouse LD50 intraperitoneal 600mg/kg (600mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 1439, 1974.
mouse LD50 oral 5600mg/kg (5600mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Oyo Yakuri. Pharmacometrics. Vol. 9, Pg. 387, 1975.
mouse LD50 subcutaneous 3170mg/kg (3170mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE Sapporo Igaku Zasshi. Sapporo Medical Journal. Vol. 3, Pg. 73, 1952.
mouse LDLo intraduodenal 1gm/kg (1000mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 1439, 1974.
rabbit LD50 skin > 5gm/kg (5000mg/kg)   Food and Cosmetics Toxicology. Vol. 13, Pg. 825, 1975.
rat LD50 intraperitoneal 3600mg/kg (3600mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Oyo Yakuri. Pharmacometrics. Vol. 9, Pg. 387, 1975.
rat LD50 intravenous 110mg/kg (110mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Oyo Yakuri. Pharmacometrics. Vol. 9, Pg. 387, 1975.
rat LD50 oral 4400mg/kg (4400mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Oyo Yakuri. Pharmacometrics. Vol. 9, Pg. 387, 1975.
rat LDLo subcutaneous 30200mg/kg (30200mg/kg) BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Oyo Yakuri. Pharmacometrics. Vol. 9, Pg. 387, 1975.

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