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D-limonene
Conditions | Yield |
---|---|
With ammonia; lithium | 80% |
L-carveol
D-limonene
Conditions | Yield |
---|---|
With 2-nitrobenzenesulfonyl hydrazide; triphenylphosphine; diethylazodicarboxylate In various solvent(s) -30 deg, 1 h; 23 deg C 30 min; | 78% |
Conditions | Yield |
---|---|
With triethylsilane; lithium perchlorate In diethyl ether for 16h; Ambient temperature; | 68% |
D-limonene
Conditions | Yield |
---|---|
With aluminum amalgam In tetrahydrofuran; water at 20℃; for 4h; | 58% |
D-limonene
Conditions | Yield |
---|---|
With acetic acid at 120℃; | 22% |
Conditions | Yield |
---|---|
With fired clay at 25℃; | |
With fired clay; acetic anhydride; acetic acid at 10℃; | |
With fired clay; acetic anhydride; acetic acid at 25℃; |
Pinene
2,4,6-Trinitrophenol
benzene
A
D-limonene
C
(+)-camphene
D
limonene.
Conditions | Yield |
---|---|
at 120℃; d-α-pinene; |
2-Benzoylbenzoic acid
(+)-α-pinene
formamide
D-limonene
Conditions | Yield |
---|---|
at 140℃; |
2-Benzoylbenzoic acid
(1R,5R)-(+)-β-pinene
formamide
D-limonene
Conditions | Yield |
---|---|
at 140℃; |
(R)-(+)-binaphthol mononeryl ether
A
Terpinolene
B
D-limonene
C
(-)-(S)-limonene
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; tri-tert-butylphenol; diisobutylaluminium hydride 2.) 3 h, -130 deg C, CCl3F; Yield given. Multistep reaction. Yields of byproduct given; |
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%.
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%.
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. |