(R)-(+)-Limonene supplier | CasNO.5989-27-5

Name
D-Limonene
EINECS 227-813-5
CAS No. 5989-27-5
Article Data46
CAS DataBase
Density 0.834 g/cm³
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
Hazard Symbols Xi, N
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;
PSA 0.00000
LogP 3.30890

Synthetic route

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

: 5989-27-5
D-limonene

Conditions

Conditions	Yield
With ammonia; lithium	80%

: 308363-12-4
L-carveol

: 5989-27-5
D-limonene

Conditions

Conditions	Yield
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

Conditions	Yield
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

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

: C16H27BO2

: 5989-27-5
D-limonene

Conditions

Conditions	Yield
With acetic acid at 120℃;	22%

: 7785-70-8
(+)-α-pinene

: 5989-27-5
D-limonene

Conditions

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℃;

: 80-56-8, 177698-18-9
Pinene

: 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

Conditions	Yield
at 120℃; d-α-pinene;

...Expand

: 85-52-9
2-Benzoylbenzoic acid

: 7785-70-8
(+)-α-pinene

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

: 5989-27-5
D-limonene

Conditions

Conditions	Yield
at 140℃;

...Expand

: 85-52-9
2-Benzoylbenzoic acid

: 127-91-3
(1R,5R)-(+)-β-pinene

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

: 5989-27-5
D-limonene

Conditions

Conditions	Yield
at 140℃;

...Expand

: 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

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;

...Expand

: 86851-45-8
(R)-(+)-binaphthol mononeryl ether

A: 5989-27-5
D-limonene

B: 5989-54-8
(-)-(S)-limonene

Conditions

Conditions	Yield
With (2,4,6-tri-tert-butylphenoxy)-isobutylaluminium trifluormethanesulfonate In trichlorofluoromethane at -130℃; for 3h; further reagents; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

: 130814-75-4
(-)-{1-(R)-[(1E)-2-methylbuta-1,3-dienyloxy]ethyl}benzene

: 78-79-5
isoprene

A: 5989-27-5
D-limonene

B: 18383-51-2
(-)-trans-carveol

C: 2102-58-1
(+)-trans-carveol

D: 5989-54-8
(-)-(S)-limonene

Conditions

Conditions	Yield
at 50℃; under 135011 Torr; for 60h; Product distribution; other conditions; other 1-(1-arylalkoxy)-2-methyl-1,3-butadienes; enantioselectivity of the reaction;

...Expand

: 136476-14-7
[(S)-2,2-Dimethyl-1-((E)-2-methyl-buta-1,3-dienyloxy)-propyl]-benzene

: 78-79-5
isoprene

A: 5989-27-5
D-limonene

B: 18383-51-2
(-)-trans-carveol

C: 2102-58-1
(+)-trans-carveol

D: 5989-54-8
(-)-(S)-limonene

Conditions

Conditions	Yield
at 50℃; under 135011 Torr; for 60h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 175522-76-6
[(R)-2,2-Dimethyl-1-((E)-2-methyl-buta-1,3-dienyloxy)-propyl]-benzene

: 78-79-5
isoprene

A: 5989-27-5
D-limonene

B: 18383-51-2
(-)-trans-carveol

C: 2102-58-1
(+)-trans-carveol

D: 5989-54-8
(-)-(S)-limonene

Conditions

Conditions	Yield
at 50℃; under 135011 Torr; for 60h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 136476-12-5
[(S)-2-Methyl-1-((E)-2-methyl-buta-1,3-dienyloxy)-propyl]-benzene

: 78-79-5
isoprene

A: 5989-27-5
D-limonene

B: 18383-51-2
(-)-trans-carveol

C: 2102-58-1
(+)-trans-carveol

D: 5989-54-8
(-)-(S)-limonene

Conditions

Conditions	Yield
at 50℃; under 135011 Torr; for 60h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: Benzyl-methyl-[2-((R)-4-methyl-cyclohex-3-enyl)-propyl]-amine

: 5989-27-5
D-limonene

Conditions

Conditions	Yield
With dihydrogen peroxide In tert-butyl alcohol 1.) 25 deg C, 110 h, 2.) 150 deg C, 1 torr, 1 h; Yield given;

: 67-56-1
methanol

: 5718-75-2
(1R,4R,5R)-4,7,7-trimethyl-6-thiabicyclo[3.2.1]octane

Raney nickel: Raney nickel

A: 1678-82-6
trans-1,4-menthane

B: 6069-98-3
cis-1-isopropyl-4-methyl-cyclohexane

C: 5989-27-5
D-limonene

D: 1195-31-9
(+)-p-menth-1-ene

...Expand

: 126-91-0
linalool

Japanese acid earth: Japanese acid earth

A: 123-35-3
7-methyl-3-methene-1,6-octadiene

B: 106-24-1
Geraniol

C: 98-55-5
terpineol

D: 5989-27-5
D-limonene

Conditions

Conditions	Yield
at 159℃;

...Expand

: 64-18-6
formic acid

: 80-56-8, 177698-18-9
Pinene

A: 586-62-9
Terpinolene

B: 5989-27-5
D-limonene

C: 138-86-3
limonene.

D terpinene: terpinene

Conditions

Conditions	Yield
d-α-pinene;

...Expand

: 60-29-7
diethyl ether

: 4764-54-9
1,2,8,9-tetrabromo-p-menthane

: 7553-56-2
iodine

magnesium: magnesium

: 5989-27-5
D-limonene

Conditions

Conditions	Yield
at 0℃; d-limonene tetrabromide;

...Expand

: 64-17-5
ethanol

: 4764-54-9
1,2,8,9-tetrabromo-p-menthane

zinc dust: zinc dust

: 5989-27-5
D-limonene

Conditions

Conditions	Yield
d-limonene tetrabromide;

...Expand

: 7785-70-8
(+)-α-pinene

aluminium silicate: aluminium silicate

A: 5989-27-5
D-limonene

B: 79-92-5
(+)-camphene

Conditions

Conditions	Yield
Mechanism;

...Expand

: 7785-70-8
(+)-α-pinene

titanic acid: titanic acid

A: 5989-27-5
D-limonene

B: 79-92-5
(+)-camphene

Conditions

Conditions	Yield
Mechanism;

...Expand

: 7785-70-8
(+)-α-pinene

: 64-19-7
acetic acid

fired clay: fired clay

A: 98-55-5
terpineol

B: 5989-27-5
D-limonene

: 6627-72-1
rac-endo-borneol

D: 507-70-0
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol

Conditions

Conditions	Yield
at 30℃; anschl. Verseifen;

...Expand

: 7785-70-8
(+)-α-pinene

fired clay: fired clay

A: 5989-27-5
D-limonene

B: 79-92-5
(+)-camphene

C: 138-86-3
limonene.

Conditions

Conditions	Yield
at 10℃;

...Expand

: 131348-01-1
(1S)-endo-fenchylamine

: 64-19-7
acetic acid

sodium nitrite: sodium nitrite

A: 5989-27-5
D-limonene

B: 116724-26-6
α-fenchene

C: 488-97-1
(+)-cyclofenchene

D (-)-ξ-fenchene: (-)-ξ-fenchene

Conditions

Conditions	Yield
Produkt 5: (+)-α-Terpineol, Produkt 6: (-)-α-Fenchol, Produkt 7: (-)-β-Fenchol und Produkt 8: (-)-α-Fenchenhydrat;

...Expand

: phthalic acid mono-((R)-p-menth-1-en-8-yl ester)

aqueous NaOH-solution: aqueous NaOH-solution

A: 5989-27-5
D-limonene

B d-α-terpineol: d-α-terpineol

Conditions

Conditions	Yield
bei der Wasserdampfdestillation;

...Expand

: 39864-10-3
α-terpinyl chloride

A: 586-62-9
Terpinolene

B: 5989-27-5
D-limonene

C: 5989-54-8
(-)-(S)-limonene

Conditions

Conditions	Yield
With 2,4,6-trimethyl-pyridine for 8h; Heating; Title compound not separated from byproducts;

...Expand

: 2-Benzyloxy-2'-((Z)-3,7-dimethyl-octa-2,6-dienyloxy)-[1,1']binaphthalenyl

A: 99-86-5
1-methyl-4-isopropyl-1,3-cyclohexadiene

B: 39864-10-3
α-terpinyl chloride

C: 5989-27-5
D-limonene

D: 5989-54-8
(-)-(S)-limonene

Conditions

Conditions	Yield
With tin(IV) chloride In various solvent(s) at -78℃; for 12h; Product distribution; Further Variations:; Solvents; Reagents; Temperatures; time;

...Expand

: 2'-((Z)-3,7-Dimethyl-octa-2,6-dienyloxy)-2-(4-trifluoromethyl-benzyloxy)-[1,1']binaphthalenyl

A: 39864-10-3
α-terpinyl chloride

B: 5989-27-5
D-limonene

C: 5989-54-8
(-)-(S)-limonene

Conditions

Conditions	Yield
With tin(ll) chloride In dichloromethane at -97℃; for 6h; Product distribution; Further Variations:; Solvents; Temperatures; time;

...Expand

: 5989-27-5
D-limonene

: 1195-31-9
(+)-p-menth-1-ene

Conditions

Conditions	Yield
With iron(III) chloride; lithium aluminium tetrahydride; hydrogen In tetrahydrofuran at 18℃; under 7500.75 Torr; for 20h; Inert atmosphere; Sealed tube;	100%
With ethanol; lithium; nickel dichloride; 4,4'-di-tert-butylbiphenyl In tetrahydrofuran at 20℃; for 22h;	99%
With platinum(IV) oxide; hydrogen under 775.743 Torr; regioselective reaction;	99%

: 5989-27-5
D-limonene

: 1195-92-2
(4R)-limonene 1,2-epoxide

Conditions

Conditions	Yield
With urea hydrogen peroxide adduct; methyltrioxorhenium(VII) In dichloromethane at 20℃; for 0.5h;	99%
With tert.-butylhydroperoxide In decane at 55℃; for 3h; in air; regioselective reaction;	95%
With C15H34N(1+)*H2O4P(1-); Tri(dodecyltrimethylammonium) dodecatungstophosphate; dihydrogen peroxide In water; toluene at 65℃; for 6h; Inert atmosphere;	95%

: 5989-27-5
D-limonene

: C37H48N2O4S3

: C47H64N2O4S3

Conditions

Conditions	Yield
With fac-tris(2-phenylpyridinato-N,C2')iridium(III) In toluene at 20℃; for 36h; Sealed tube; Irradiation; Inert atmosphere;	99%

: 5989-27-5
D-limonene

: 4680-24-4
cis-(R)-limonene oxide

Conditions

Conditions	Yield
With dihydrogen peroxide; polystyrene; {2-(aminomethyl)pyridine}methyl(trioxo)rhenium(VII) In dichloromethane; water; acetonitrile at -10℃; for 2h;	98%
With dihydrogen peroxide; divinylbenzene cross-linked poly(4-vinylpyridine); methyltrioxorhenium(VII) In dichloromethane; water; acetonitrile at 25℃; for 1.5h;	89%
Multi-step reaction with 2 steps 1: bis[(4R)-2(4-Et-3,4-dihydro-2-oxazolyl)phenolato-N,O]O(O2)Mo; aq. tert-butyl hydroperoxide / toluene / 22 h / 20 °C 2: (μ-O)[MoO2(NCS)-2-(3,4-dihydro-4-MeOMe-oxazolyl-Ph)Py-N,N]2; aq. tert-butyl hydroperoxide / toluene / 22 h / 20 °C View Scheme

: 5989-27-5
D-limonene

: (R)-5-Isopropenyl-2-methylene-cyclohexyl-hydroperoxide

Conditions

Conditions	Yield
With zeolite NaY; oxygen Irradiation; photooxygenation;	97%

: 5989-27-5
D-limonene

: 775-12-2
diphenylsilane

: (2-((R)-4-methylcyclohex-3-en-1-yl)propyl)diphenylsilane

Conditions

Conditions	Yield
Stage #1: diphenylsilane With [(2-dicyclohexylphosphinocyclopentene-1-(2,6-dimethylphenyl)imine)Ni(allyl)]OTf In benzene-d6 at 20℃; for 0.0833333h; Inert atmosphere; Glovebox; Stage #2: D-limonene In benzene-d6 at 20℃; for 12h; Inert atmosphere; Sealed tube;	97%
With [N,N'-(1,2-dimethyl-1,2-ethanediylidene)bis[3-(diphenylphosphino)-1-propanamine]]Ni In benzene-d6 at 70℃; for 168h; Inert atmosphere;	76%

: 5989-27-5
D-limonene

: 694-53-1
phenylsilane

: (4R)-1-methyl-4-[(1R,S)-1-methyl-2-(phenylsilyl)ethyl]cyclohex-1-ene

Conditions

Conditions	Yield
With n-butyllithium; 2,6-bis-[1-(2,6-diethylphenylimino)ethyl]pyridine iron(II) chloride In hexane; toluene at 20℃; for 1h; Inert atmosphere; regioselective reaction;	96%
Stage #1: phenylsilane With (C5Me5)(iPr2MeP)H2FeH(N2); trityl tetrakis(pentafluorophenyl)borate In fluorobenzene at -35 - 20℃; Stage #2: D-limonene In fluorobenzene at 20℃; for 20h; regioselective reaction;	92%
yttrium(pentamethylcyclopentadienyl)2CH(trimethylsilyl)2 In benzene for 96h; Ambient temperature;	61%
(η5-C5Me4(i)Pr)2YMe*THF for 96h; Product distribution; Ambient temperature; other catalysts;
With [(2,6-iPr2PhBDI)Mn(μ-H)]2 In benzene-d6 at 130℃; for 144h; Inert atmosphere;

: 5989-27-5
D-limonene

A: 184488-93-5
(R)-8,9-limonene oxide

: 203719-54-4
(1RS,2SR,4R)-limonene-1,2-epoxide

Conditions

Conditions	Yield
With 1H-imidazole; dihydrogen peroxide; sodium N-dodecanoyl-L-proplinate; Mn[5-(4-C6H4CO-(N-L-proline))-10,15,20-Ph3-porphyrinyl]Cl In ethanol; water at 25℃; for 0.166667h; Product distribution; Further Variations:; Catalysts; Reagents;	A n/a B 95%

: 5989-27-5
D-limonene

: 4497-96-5
1-Chloro-4-(1-chloro-1-methyl-ethyl)-1-methyl-cyclohexane

Conditions

Conditions	Yield
With acetyl chloride In ethanol at 30℃; for 0.166667h; Markovnikov hydrochlorination;	95%
Multi-step reaction with 2 steps 1: 250 - 270 °C 2: diethyl ether; hydrogen chloride View Scheme

: 5989-27-5
D-limonene

A: 1678-82-6
trans-1,4-menthane

B: 6069-98-3
cis-1-isopropyl-4-methyl-cyclohexane

C: 1195-31-9
(+)-p-menth-1-ene

Conditions

Conditions	Yield
With hydrogen; 2 In neat (no solvent)	A 2% B 4% C 94%
With ruthenium; hydrogen at 30℃; under 900.09 Torr; Reagent/catalyst;

...Expand

: 110-91-8
morpholine

: 201230-82-2
carbon monoxide

: 5989-27-5
D-limonene

: 4-[3-((R)-4-Methyl-cyclohex-3-enyl)-butyl]-morpholine

Conditions

Conditions	Yield
With hydrogen; chloro(1,5-cyclooctadiene)rhodium(I) dimer In acetonitrile at 80℃; under 60004.8 Torr; for 20h;	93%
Stage #1: morpholine; carbon monoxide; D-limonene With carbonylhydridetris(triphenylphosphine)rhodium(I); hydrogen In tetrahydrofuran at 100℃; Autoclave; Stage #2: With hydrogen In tetrahydrofuran at 100℃; under 30003 Torr; Autoclave;	79%

...Expand

: 5989-27-5
D-limonene

: 59121-74-3
(1S,2R,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol

Conditions

Conditions	Yield
With oxygen; potassium carbonate In water at 25℃; under 1551.49 Torr; for 72h; enantioselective reaction;	92%

: 5989-27-5
D-limonene

: 506422-90-8
2-bromo-1-hydroxy-p-menth-8-ene

Conditions

Conditions	Yield
With N-Bromosuccinimide In water; acetone at 10℃;	91%

: 5989-27-5
D-limonene

: 521925-06-4
(1S,4R)-2-chloro-4-(1-methylvinyl)-1-methylcyclohexanol

Conditions

Conditions	Yield
With sodium hypochlorite; water; copper(II) acetate monohydrate In 1,2-dichloro-ethane at 60℃; for 9h; Temperature; Solvent;	90.2%

: 5989-27-5
D-limonene

: 61585-35-1
p-menth-1-ene

Conditions

Conditions	Yield
With hydrogen; platinum on activated charcoal pressure of 60 lb/sq in. to 43.5 lb/sq in.;	90%
With copper at 200℃; inactive substances;
With hydrogen; platinum dihydrolimonene;
With sodium tetrahydroborate In methanol at 20℃; Catalytic behavior; Reagent/catalyst; Inert atmosphere;

: 5989-27-5
D-limonene

: 6252-33-1
4-isopropenyl-1-methylcyclohexane

Conditions

Conditions	Yield
Stage #1: D-limonene With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 0 - 25℃; for 2.5h; Inert atmosphere; Stage #2: With palladium 10% on activated carbon; hydrogen In tetrahydrofuran under 760.051 Torr; Inert atmosphere; Stage #3: With 2-methyl-2-nitrosopropane dimer In tetrahydrofuran for 0.75h; regioselective reaction;	90%

: 64-17-5
ethanol

: 201230-82-2
carbon monoxide

: 5989-27-5
D-limonene

A: (Ξ)-3-((R)-4-methyl-cyclohex-3-enyl)-butyraldehyde diethylacetal

B: 199445-85-7
3-(4-methylcyclohex-3-enyl)butanal

Conditions

Conditions	Yield
With methoxy(cyclooctadiene)rhodium(I) dimer; tri(o-t-butylphenyl)phosphite; hydrogen at 80℃; under 60804.1 Torr; for 4h; Inert atmosphere; Autoclave;	A 90% B n/a

...Expand

: 5989-27-5
D-limonene

: 287720-47-2
(2RS)-2-<(1R)-4-methylcyclohex-3-enyl>propanol

Conditions

Conditions	Yield
Stage #1: D-limonene With PS-9-BBN In tetrahydrofuran at 40℃; for 24h; Stage #2: With tetra(n-butyl)ammonium hydroxide; dihydrogen peroxide In tetrahydrofuran; methanol at 0 - 50℃; for 4h;	89%
Stage #1: D-limonene With 9-bora-bicyclo[3.3.1]nonane at 20℃; Inert atmosphere; Stage #2: With dihydrogen peroxide; sodium hydroxide In ethanol at 50℃; for 2h;	89.6%
Stage #1: D-limonene With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 20℃; for 2h; Stage #2: With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran; water temp. < 10 deg C; Stage #3: In tetrahydrofuran; water at 40℃; for 2h;	80%

: 5989-27-5
D-limonene

: 99-87-6
4-methylisopropylbenzene

Conditions

Conditions	Yield
With palladium 10% on activated carbon at 140℃; for 1h;	89%
With iodine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene for 0.75h; Reflux;	82%
With dodecane; hydrogen at 300℃; under 11251.1 Torr; for 2h; Catalytic behavior; Temperature; Autoclave; Inert atmosphere;	57%

: 110-85-0
piperazine

: 201230-82-2
carbon monoxide

: 5989-27-5
D-limonene

: 1098145-03-9
C15H28N2

Conditions

Conditions	Yield
Stage #1: piperazine; carbon monoxide; D-limonene With carbonylhydridetris(triphenylphosphine)rhodium(I); hydrogen In tetrahydrofuran at 100℃; Autoclave; Stage #2: With hydrogen In tetrahydrofuran at 100℃; under 30003 Torr; Autoclave;	89%

...Expand

: 5989-27-5
D-limonene

: (1S,2S,4R)-2-bromo-1-methyl-4-(prop-1-en-2-yl)cyclohexanol

Conditions

Conditions	Yield
With sodium hypobromide; copper(II) acetate monohydrate In water; 1,2-dichloro-ethane at 80℃; for 6h; Reagent/catalyst; Temperature;	88.3%
With N-Bromosuccinimide; water In acetone at 0 - 5℃;	85%
With N-Bromosuccinimide; water In acetone at 0 - 25℃; for 1h; Large scale; chemoselective reaction;
With N-Bromosuccinimide In water; acetone at 0 - 25℃; for 1h;
With N-Bromosuccinimide In water; acetone at 0℃; for 0.666667h; Inert atmosphere; Schlenk technique; Glovebox;

: 5989-27-5
D-limonene

: 4764-54-9, 33758-94-0, 33758-98-4, 34048-93-6, 34048-94-7, 40772-56-3
(+)-limonene tetrabromide

Conditions

Conditions	Yield
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; cetyltrimethylammonim bromide In dichloromethane; chloroform	87%

: 5989-27-5
D-limonene

: 7086-79-5, 85031-77-2, 127288-10-2, 136521-14-7
(R)-4-methyl-3-(3'-oxobutyl)pent-4-enal

Conditions

Conditions	Yield
Stage #1: D-limonene With pyridine; ozone In methanol at -50℃; for 12h; Inert atmosphere; Stage #2: With dimethylsulfide In methanol at -50℃;	86%
Stage #1: D-limonene With oxygen; ozone In methanol; dichloromethane at -70℃; Stage #2: With dimethylsulfide at 20℃; for 5h;	70%
Stage #1: D-limonene With ozone In methanol; dichloromethane at -70℃; Stage #2: With dimethylsulfide In methanol; dichloromethane at 20℃; for 5h;	70%

: 5989-27-5
D-limonene

: 504-02-9
1,3-cylohexanedione

: (1'R,2RS)-2-methyl-2-(4'-methylcyclohex-3'-enyl)-2,3,5,6,7-pentahydrobenzo[1,2-b]furan-4-one

Conditions

Conditions	Yield
With manganese triacetate; acetic acid at 70℃; for 2h;	86%

: 5989-27-5
D-limonene

: 123-54-6
acetylacetone

: (1'R,5RS)-3-acetyl-2,5-dimethyl-5-(4'-methylcyclohex-3'-enyl)-4,5-dihydrofuran

Conditions

Conditions	Yield
With manganese triacetate; acetic acid at 70℃; for 1.5h;	86%

: 5989-27-5
D-limonene

: 93-91-4
1-phenylbutan-1,3-dione

: [2,5-Dimethyl-5-((R)-4-methyl-cyclohex-3-enyl)-4,5-dihydro-furan-3-yl]-phenyl-methanone

Conditions

Conditions	Yield
With manganese triacetate; acetic acid at 70℃; for 1.5h;	86%

: 5989-27-5
D-limonene

A: 99-82-1, 1678-82-6, 6069-98-3, 129939-70-4, 129939-71-5
Menthane

B: 1195-31-9
(+)-p-menth-1-ene

Conditions

Conditions	Yield
With platinum(IV) oxide; hydrogen at 20℃; under 760.051 Torr; Overall yield = 16 g;	A n/a B 85%
With (bis-1,2-diphenylphosphinoethane)Co(CH2SiMe3)2; hydrogen In benzene at 25℃; under 3040.2 Torr; for 6h; Time;	A 55% B 42%
With hydrogen; platinum(IV) oxide In methanol under 760 Torr; below 20 deg C; Yield given. Yields of byproduct given;
With platinum(IV) oxide; hydrogen In ethanol at 20℃; under 760.051 Torr; for 5.4h;

: 5989-27-5
D-limonene

: 184488-93-5
(R)-8,9-limonene oxide

Conditions

Conditions	Yield
With perchloric acid; dihydrogen peroxide In water; acetonitrile; tert-butyl alcohol at 60℃; for 0.166667h; stereoselective reaction;	85%
With fluorapatite; dihydrogen peroxide; tris(cetylpyridinium) 12-tungstophosphate In water at 25℃; for 14h;	61%
With tert.-butylhydroperoxide In water; acetonitrile at 70℃; for 24h;	35%

: 5989-27-5
D-limonene

: 107-56-2
O,O-diisopropyl hydrogen phosphorodithioate

: O,O-diisopropyl S-[1-methyl-1-(4-methylcyclohex-3-en-1-yl)ethyl]dithiophosphate

Conditions

Conditions	Yield
With zinc(II) chloride at 20℃; for 2h;	85%
With zinc(II) chloride at 20℃; Inert atmosphere;	85%
With zinc(II) chloride

: 107-10-8
propylamine

: 201230-82-2
carbon monoxide

: 5989-27-5
D-limonene

: 1098144-84-3
C14H27N

Conditions

Conditions	Yield
Stage #1: propylamine; carbon monoxide; D-limonene With carbonylhydridetris(triphenylphosphine)rhodium(I); hydrogen In tetrahydrofuran at 100℃; Autoclave; Stage #2: With hydrogen In tetrahydrofuran at 100℃; under 30003 Torr; Autoclave;	85%

...Expand

(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%.

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.

Product Name

D-Limonene

Synthetic route

(R)-(+)-Limonene Specification

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