(-)-beta-Citronellol supplier

Name
BETA-RHODINOL
EINECS 231-415-7
CAS No. 7540-51-4
Article Data61
CAS DataBase
Density 0.845 g/cm³
Solubility SLIGHTLY SOLUBLE
Melting Point 77-83oC(lit.)
Formula C₁₀H₂₀O
Boiling Point 224.5 °C at 760 mmHg
Molecular Weight 156.268
Flash Point 98.3 °C
Transport Information
Appearance Clear colorless liquid
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 6-Octen-1-ol,3,7-dimethyl-, (-)- (8CI);6-Octen-1-ol, 3,7-dimethyl-, (S)-;(-)-(S)-Citronellol;(-)-Citronellol;(-)-b-Citronellol;(S)-(-)-Citronellol;(S)-(-)-b-Citronellol;(S)-3,7-Dimethyl-6-octen-1-ol;(S)-Citronellol;(S)-b-Citronellol;L-Citronellol;
PSA 20.23000
LogP 2.75130

Synthetic route

: 106-24-1
Geraniol

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With bis(norbornadiene)rhodium(l)tetrafluoroborate; (RC,SFc,SP)-1-[2-(1-N,N-dimethylaminoethyl)ferrocen-1-yl]phenylphosphino-1'-dicyclohexylphosphinoferrocene; hydrogen In dichloromethane at 20℃; under 19001.3 Torr; for 20h; Inert atmosphere; Autoclave; enantioselective reaction;	99%
With [RuCl(p-cymene)((R)-Tol-BINAP)]Cl; potassium hydroxide In isopropyl alcohol for 2h; Inert atmosphere; Reflux;	70%
Multi-step reaction with 2 steps 1: in Ficus retusa Linn. 2: in Ficus retusa Linn. nach Injektion View Scheme

: 141-27-5
3,7-dimethyl-2,6-octadienal

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With dichloro(1,5-cyclooctadiene)ruthenium(II); (R)-(+)-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine; niobium pentachloride; HSiPh3 In toluene at 40℃; for 3h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Glovebox; Sealed tube; Inert atmosphere; enantioselective reaction;	98.59%
With (η4-cyclooctadiene)((R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl)rhodium(I) tetrfluoroborate; hydrogen In methanol at 60℃; under 33753.4 Torr; for 5h; Autoclave; enantioselective reaction;	88%

: Carbonic acid (S)-3,7-dimethyl-oct-6-enyl ester 2,2,2-trichloro-ethyl ester

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With indium; water; ammonium chloride In methanol for 1h; Heating;	98%

: 5949-05-3
(S)-Citronellal

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether	96%
With lithium aluminium tetrahydride In diethyl ether	94%
With sodium tetrahydroborate In ethanol at 0℃;	93%

: Trichloro-acetic acid (S)-3,7-dimethyl-oct-6-enyl ester

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With indium; water; ammonium chloride In methanol for 0.5h; Heating;	95%

: (R)-2-(3,7-dimethyloct-6-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With sodium perborate; water In tetrahydrofuran at 20℃; for 4h; enantioselective reaction;	95%

: 93041-00-0
2,2-dimethyl-propionic acid (3S)-3,7-dimethyl-oct-6-enyl ester

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With sodium hydroxide In methanol Ambient temperature;	94%

: (S)-8-(allyloxy)-2,6-dimethyloct-2-ene

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
Stage #1: (S)-8-(allyloxy)-2,6-dimethyloct-2-ene With C12H37NiP4(1+)*C2F6NO4S2(1-) In tetrahydrofuran at 20℃; for 0.5h; Glovebox; Schlenk technique; Inert atmosphere; Stage #2: With toluene-4-sulfonic acid In tetrahydrofuran for 1.5h; Glovebox; Schlenk technique; Reflux; Inert atmosphere;	94%

: 89156-40-1
(S)-3,7-Dimethyl-oct-6-enoic acid (1S,2R,3S,4R)-3-(2,2-dimethyl-propoxy)-4,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester

A: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

B: 85695-96-1
(1R,2S,3R,4S)-2-(2,2-dimethylpropoxy)-1,7,7-trimethylbicyclo<2.2.1>heptan-3-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride	A 88% B 81%

: 84237-05-8
(S)-((3,7-dimethyloct-6-enyloxy)methyl)benzene

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With ammonia; lithium In tetrahydrofuran at -30℃; for 0.666667h;	82%

: (S)-8-(2,3-dimethyl-but-2-en-1-yloxy)-2,6-dimethyloct-2-ene

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With (PhSO2)2; water In dichloromethane at 80℃;	82%

: 5949-05-3
(S)-Citronellal

A: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

B: 2111-53-7
(S)-(-)-citronellic acid

Conditions

Conditions	Yield
With Fusarium concentricum In dimethyl sulfoxide at 28 - 30℃; for 120h; Reagent/catalyst; Microbiological reaction;	A 76% B 5%
With Fusarium fujikuroi In dimethyl sulfoxide at 28 - 30℃; for 120h; Microbiological reaction;	A 36% B 43%
With endosperms of Triticum aestivum L. cv Dariel wheat seeds In water at 27℃; Reagent/catalyst; Concentration; Darkness; Enzymatic reaction; enantioselective reaction;

: 106-25-2
Nerol

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; potassium hydroxide at 100℃; for 2h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	70%
With hydrogen; BINAP-Ru(II) dicarboxylate In methanol at 18 - 20℃; Yield given;
With hydrogen; BINAP-(Ru(II) dicarboxylate In methanol at 18 - 20℃; Product distribution; examination of enantioselectivity; various complexes;

: 2111-53-7
(S)-(-)-citronellic acid

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 25℃; for 3h; Inert atmosphere;	69%

: 5949-05-3
(S)-Citronellal

A: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

B: 19956-48-0
(1S,3R,4S)-p-menthane-3,8-diol

C: 3564-95-2, 3564-98-5, 19956-48-0, 42822-86-6, 81176-87-6, 81176-88-7, 91739-72-9, 91739-73-0, 92471-23-3, 107133-84-6, 138663-70-4, 140924-71-6
(1S,3S,4S)-p-menthane-3,8-diol

D (−)-neo-isopulegol: 122517-60-6
(−)-neo-isopulegol

E (+)-isopulegol: (+)-isopulegol

Conditions

Conditions	Yield
With Penicillium paxilli In dimethyl sulfoxide at 28 - 30℃; for 120h; Microbiological reaction;	A 10% B 50% C 20% D 5% E 2%

...Expand

(S)-citronellyl propionate: (S)-citronellyl propionate

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With potassium chloride; water In acetone	48%

: 106-23-0, 26489-02-1
3,7-dimethyl-oct-6-enal

A: 2385-77-5
(R)-Citronellal

B: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With baker's yeast	A 21% B 33%

: (S)-(-)-3,7-dimethyl-6-ocyten-1-yl diphenylmethylsilyl ether

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With potassium (4-methylphenyl)trifluoroborate In dimethyl sulfoxide at 37℃; for 24h; Inert atmosphere;	18%

: 64-17-5
ethanol

: 5949-05-3
(S)-Citronellal

: EtOMgCl

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

...Expand

: 5392-40-5
(E/Z)-3,7-dimethyl-2,6-octadienal

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
in Ficus retusa Linn. nach Injektion;

: 106-25-2
Nerol

A: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

B: 1117-61-9
(3R)-citronellol

Conditions

Conditions	Yield
With hydrogen; <(+)-CyBINAP>-RhN In benzene under 15200 Torr; Ambient temperature; Yield given. Yields of byproduct given;
With hydrogen; ClO4 In benzene under 7600 Torr; for 8h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With hydrogen; Ru2Cl4-((S)-2,2'-bis[di(p-tolyl)phosphino]-1,1'-binaphthyl)2NEt3 In methanol at 19.9℃; under 1807.6 Torr; Product distribution; different pressure and temperature;
With 1,2-bis(2,5-diisopropylphospholano)benzene; potassium hydroxide at 100℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;

: 106-24-1
Geraniol

A: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

B: 1117-61-9
(3R)-citronellol

C: 1117-60-8
(R)-3,7-dimethyloctan-1-ol

Conditions

Conditions	Yield
With hydrogen; {RuI((R)-2,2'-bis(diphenylphospino)-1,1'-binaphthyl)(p-cymene)}I In methanol; water at 20℃; under 76000 Torr; for 8h; Yield given. Yields of byproduct given;

...Expand

: 106-24-1
Geraniol

A: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

B: 1117-61-9
(3R)-citronellol

Conditions

Conditions	Yield
With <<(-)-2,2'-bis(diphenylphosphino)-4,4',6,6'-tetramethyl-3,3'-bibenzothiophene>Ru(p-cumene)I>I; hydrogen In methanol at 25℃; under 7355.08 Torr; for 88h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With ((S)-(6,6'-dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine))Ru(O2CCF3)2; hydrogen In methanol at 20 - 25℃; under 45003.6 Torr; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With hydrogen; <(+)-BINAP>RhN In benzene under 22800 Torr; Ambient temperature; Yield given. Yields of byproduct given;

: (R)-1-[(R)-3-(1-Hydroxy-1-methyl-ethyl)-pyrrolidin-1-yl]-3,7-dimethyl-oct-6-en-1-one

A: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

B: 1117-61-9
(3R)-citronellol

Conditions

Conditions	Yield
With lithium triethylborohydride In tetrahydrofuran Ambient temperature; Yield given;
With lithium triethylborohydride In tetrahydrofuran Ambient temperature; Yields of byproduct given;

: 67392-54-5
N,N-diethyl-N-{1-[(3S),7-dimethylocta-1,6-dienyl]}amine

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With oxonium; hydrogen

: 2436-90-0
(S)-(+)-dihydromyrcene

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate; 2-methyl-but-2-ene; boron trifluoride; dihydrogen peroxide 1.) THF, room temp., 3 h.; 2.) 50 deg C, 1.5 h; Multistep reaction;

: 13066-51-8
γ-geraniol

A: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

B: 1117-61-9
(3R)-citronellol

Conditions

Conditions	Yield
With Ru2Cl4-((S)-2,2'-bis[di(p-tolyl)phosphino]-1,1'-binaphthyl)2NEt3; hydrogen In methanol at 19.9℃; under 3750.3 Torr; Title compound not separated from byproducts;
With hydrogen; Ru2Cl4-((S)-2,2'-bis[di(p-tolyl)phosphino]-1,1'-binaphthyl)2NEt3 In methanol at 19.9℃; under 1807.6 Torr; Product distribution; other pressure and temperature;
With 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; potassium hydroxide at 100℃; for 6h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;

: 67601-05-2
(3S)-3,7-dimethyl-6-octen-1-yl acetate

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
Stage #1: (3S)-3,7-dimethyl-6-octen-1-yl acetate With sodium hydroxide In ethanol at 90℃; for 3h; Alkaline hydrolysis; Stage #2: With Pichia kluyveri IFO 1165 at 30℃; for 48h;

: 108-05-4
vinyl acetate

: 106-22-9
Citronellol

A: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

B: 1117-61-9
(3R)-citronellol

C: 20425-54-1
(R)-1-citronellyl acetate

D: 67601-05-2
(3S)-3,7-dimethyl-6-octen-1-yl acetate

Conditions

Conditions	Yield
With porcine pancreatic lipase In hexane for 24h; Title compound not separated from byproducts;
With porcine pancreatic lipase In hexane for 48h; Title compound not separated from byproducts;

...Expand

: 106-24-1
Geraniol

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With bis(norbornadiene)rhodium(l)tetrafluoroborate; (RC,SFc,SP)-1-[2-(1-N,N-dimethylaminoethyl)ferrocen-1-yl]phenylphosphino-1'-dicyclohexylphosphinoferrocene; hydrogen In dichloromethane at 20℃; under 19001.3 Torr; for 20h; Inert atmosphere; Autoclave; enantioselective reaction;	99%
With [RuCl(p-cymene)((R)-Tol-BINAP)]Cl; potassium hydroxide In isopropyl alcohol for 2h; Inert atmosphere; Reflux;	70%
Multi-step reaction with 2 steps 1: in Ficus retusa Linn. 2: in Ficus retusa Linn. nach Injektion View Scheme

: 141-27-5
3,7-dimethyl-2,6-octadienal

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With dichloro(1,5-cyclooctadiene)ruthenium(II); (R)-(+)-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine; niobium pentachloride; HSiPh3 In toluene at 40℃; for 3h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Glovebox; Sealed tube; Inert atmosphere; enantioselective reaction;	98.59%
With (η4-cyclooctadiene)((R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl)rhodium(I) tetrfluoroborate; hydrogen In methanol at 60℃; under 33753.4 Torr; for 5h; Autoclave; enantioselective reaction;	88%

: Carbonic acid (S)-3,7-dimethyl-oct-6-enyl ester 2,2,2-trichloro-ethyl ester

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With indium; water; ammonium chloride In methanol for 1h; Heating;	98%

: 5949-05-3
(S)-Citronellal

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether	96%
With lithium aluminium tetrahydride In diethyl ether	94%
With sodium tetrahydroborate In ethanol at 0℃;	93%

: Trichloro-acetic acid (S)-3,7-dimethyl-oct-6-enyl ester

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With indium; water; ammonium chloride In methanol for 0.5h; Heating;	95%

: (R)-2-(3,7-dimethyloct-6-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With sodium perborate; water In tetrahydrofuran at 20℃; for 4h; enantioselective reaction;	95%

: 93041-00-0
2,2-dimethyl-propionic acid (3S)-3,7-dimethyl-oct-6-enyl ester

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With sodium hydroxide In methanol Ambient temperature;	94%

: (S)-8-(allyloxy)-2,6-dimethyloct-2-ene

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
Stage #1: (S)-8-(allyloxy)-2,6-dimethyloct-2-ene With C12H37NiP4(1+)*C2F6NO4S2(1-) In tetrahydrofuran at 20℃; for 0.5h; Glovebox; Schlenk technique; Inert atmosphere; Stage #2: With toluene-4-sulfonic acid In tetrahydrofuran for 1.5h; Glovebox; Schlenk technique; Reflux; Inert atmosphere;	94%

: 89156-40-1
(S)-3,7-Dimethyl-oct-6-enoic acid (1S,2R,3S,4R)-3-(2,2-dimethyl-propoxy)-4,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester

A: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

B: 85695-96-1
(1R,2S,3R,4S)-2-(2,2-dimethylpropoxy)-1,7,7-trimethylbicyclo<2.2.1>heptan-3-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride	A 88% B 81%

: 84237-05-8
(S)-((3,7-dimethyloct-6-enyloxy)methyl)benzene

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With ammonia; lithium In tetrahydrofuran at -30℃; for 0.666667h;	82%

: (S)-8-(2,3-dimethyl-but-2-en-1-yloxy)-2,6-dimethyloct-2-ene

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With (PhSO2)2; water In dichloromethane at 80℃;	82%

: 5949-05-3
(S)-Citronellal

A: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

B: 2111-53-7
(S)-(-)-citronellic acid

Conditions

Conditions	Yield
With Fusarium concentricum In dimethyl sulfoxide at 28 - 30℃; for 120h; Reagent/catalyst; Microbiological reaction;	A 76% B 5%
With Fusarium fujikuroi In dimethyl sulfoxide at 28 - 30℃; for 120h; Microbiological reaction;	A 36% B 43%
With endosperms of Triticum aestivum L. cv Dariel wheat seeds In water at 27℃; Reagent/catalyst; Concentration; Darkness; Enzymatic reaction; enantioselective reaction;

: 106-25-2
Nerol

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; potassium hydroxide at 100℃; for 2h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	70%
With hydrogen; BINAP-Ru(II) dicarboxylate In methanol at 18 - 20℃; Yield given;
With hydrogen; BINAP-(Ru(II) dicarboxylate In methanol at 18 - 20℃; Product distribution; examination of enantioselectivity; various complexes;

: 2111-53-7
(S)-(-)-citronellic acid

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 25℃; for 3h; Inert atmosphere;	69%

: 5949-05-3
(S)-Citronellal

A: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

B: 19956-48-0
(1S,3R,4S)-p-menthane-3,8-diol

C: 3564-95-2, 3564-98-5, 19956-48-0, 42822-86-6, 81176-87-6, 81176-88-7, 91739-72-9, 91739-73-0, 92471-23-3, 107133-84-6, 138663-70-4, 140924-71-6
(1S,3S,4S)-p-menthane-3,8-diol

D: 122517-60-6
(−)-neo-isopulegol

E: 104870-56-6
(+)-isopulegol

Conditions

Conditions	Yield
With Penicillium paxilli In dimethyl sulfoxide at 28 - 30℃; for 120h; Microbiological reaction;	A 10% B 50% C 20% D 5% E 2%

...Expand

: (S)-citronellyl propionate

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With potassium chloride; water In acetone	48%

: 106-23-0, 26489-02-1
3,7-dimethyl-oct-6-enal

A: 2385-77-5
(R)-Citronellal

B: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With baker's yeast	A 21% B 33%

: (S)-(-)-3,7-dimethyl-6-ocyten-1-yl diphenylmethylsilyl ether

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With potassium (4-methylphenyl)trifluoroborate In dimethyl sulfoxide at 37℃; for 24h; Inert atmosphere;	18%

: 64-17-5
ethanol

: 5949-05-3
(S)-Citronellal

: EtOMgCl

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

...Expand

: 5392-40-5
(E/Z)-3,7-dimethyl-2,6-octadienal

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
in Ficus retusa Linn. nach Injektion;

: 106-25-2
Nerol

A: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

B: 1117-61-9
(3R)-citronellol

Conditions

Conditions	Yield
With hydrogen; <(+)-CyBINAP>-RhN In benzene under 15200 Torr; Ambient temperature; Yield given. Yields of byproduct given;
With hydrogen; ClO4 In benzene under 7600 Torr; for 8h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With hydrogen; Ru2Cl4-((S)-2,2'-bis[di(p-tolyl)phosphino]-1,1'-binaphthyl)2NEt3 In methanol at 19.9℃; under 1807.6 Torr; Product distribution; different pressure and temperature;
With 1,2-bis(2,5-diisopropylphospholano)benzene; potassium hydroxide at 100℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;

: 106-24-1
Geraniol

A: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

B: 1117-61-9
(3R)-citronellol

C: 1117-60-8
(R)-3,7-dimethyloctan-1-ol

Conditions

Conditions	Yield
With hydrogen; {RuI((R)-2,2'-bis(diphenylphospino)-1,1'-binaphthyl)(p-cymene)}I In methanol; water at 20℃; under 76000 Torr; for 8h; Yield given. Yields of byproduct given;

...Expand

: 106-24-1
Geraniol

A: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

B: 1117-61-9
(3R)-citronellol

Conditions

Conditions	Yield
With <<(-)-2,2'-bis(diphenylphosphino)-4,4',6,6'-tetramethyl-3,3'-bibenzothiophene>Ru(p-cumene)I>I; hydrogen In methanol at 25℃; under 7355.08 Torr; for 88h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With ((S)-(6,6'-dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine))Ru(O2CCF3)2; hydrogen In methanol at 20 - 25℃; under 45003.6 Torr; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With hydrogen; <(+)-BINAP>RhN In benzene under 22800 Torr; Ambient temperature; Yield given. Yields of byproduct given;

: (R)-1-[(R)-3-(1-Hydroxy-1-methyl-ethyl)-pyrrolidin-1-yl]-3,7-dimethyl-oct-6-en-1-one

A: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

B: 1117-61-9
(3R)-citronellol

Conditions

Conditions	Yield
With lithium triethylborohydride In tetrahydrofuran Ambient temperature; Yield given;
With lithium triethylborohydride In tetrahydrofuran Ambient temperature; Yields of byproduct given;

: 67392-54-5
N,N-diethyl-N-{1-[(3S),7-dimethylocta-1,6-dienyl]}amine

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With oxonium; hydrogen

: 2436-90-0
(S)-(+)-dihydromyrcene

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate; 2-methyl-but-2-ene; boron trifluoride; dihydrogen peroxide 1.) THF, room temp., 3 h.; 2.) 50 deg C, 1.5 h; Multistep reaction;

: 13066-51-8
γ-geraniol

A: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

B: 1117-61-9
(3R)-citronellol

Conditions

Conditions	Yield
With Ru2Cl4-((S)-2,2'-bis[di(p-tolyl)phosphino]-1,1'-binaphthyl)2NEt3; hydrogen In methanol at 19.9℃; under 3750.3 Torr; Title compound not separated from byproducts;
With hydrogen; Ru2Cl4-((S)-2,2'-bis[di(p-tolyl)phosphino]-1,1'-binaphthyl)2NEt3 In methanol at 19.9℃; under 1807.6 Torr; Product distribution; other pressure and temperature;
With 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; potassium hydroxide at 100℃; for 6h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;

: 67601-05-2
(3S)-3,7-dimethyl-6-octen-1-yl acetate

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

Conditions

Conditions	Yield
Stage #1: (3S)-3,7-dimethyl-6-octen-1-yl acetate With sodium hydroxide In ethanol at 90℃; for 3h; Alkaline hydrolysis; Stage #2: With Pichia kluyveri IFO 1165 at 30℃; for 48h;

: 108-05-4
vinyl acetate

: 106-22-9
Citronellol

A: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

B: 1117-61-9
(3R)-citronellol

C: 20425-54-1
(R)-1-citronellyl acetate

D: 67601-05-2
(3S)-3,7-dimethyl-6-octen-1-yl acetate

Conditions

Conditions	Yield
With porcine pancreatic lipase In hexane for 24h; Title compound not separated from byproducts;
With porcine pancreatic lipase In hexane for 48h; Title compound not separated from byproducts;

...Expand

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

: 68680-98-8
S-(-)-dihydrocitronellol

Conditions

Conditions	Yield
With palladium on activated charcoal; hydrogen	100%
With palladium on activated charcoal; hydrogen In methanol; ethyl acetate at 25℃; for 18h; Inert atmosphere;	98%
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 0.25h; Inert atmosphere;	96%

: 7540-51-4
(S)-3,7-dimethyl-6-octen-1-ol

: 98-59-9
p-toluenesulfonyl chloride

: 41144-01-8, 67214-54-4, 93303-23-2, 116661-43-9
(S)-3,7-dimethyl-6-octenyl tosylate

Conditions

Conditions	Yield
With pyridine at 0℃; for 12h; Tosylation;	100%
With pyridine at 0℃; for 72h;	100%
With pyridine	100%

(-)-beta-Citronellol Chemical Properties

Molecular structure of 6-Octen-1-ol, 3,7-dimethyl-, (3S)- (CAS NO.7540-51-4) is:

Product Name: 6-Octen-1-ol, 3,7-dimethyl-, (3S)-
CAS Registry Number: 7540-51-4
IUPAC Name: 3,7-dimethyloct-6-en-1-ol
Molecular Weight: 156.2652 [g/mol]
Molecular Formula: C₁₀H₂₀O
XLogP3-AA: 3.2
H-Bond Donor: 1
H-Bond Acceptor: 1
EINECS: 231-415-7
Surface Tension: 28.5 dyne/cm
Density: 0.845 g/cm³
Flash Point: 98.3 °C
Enthalpy of Vaporization: 53.6 kJ/mol
Boiling Point: 224.5 °C at 760 mmHg
Vapour Pressure: 0.0183 mmHg at 25°C
Vapor pressure: ~0.02 mm Hg ( 25 °C)
Refractive index: n20/D 1.456
Storage temp.: 2-8°C
Product Categories: All Aliphatics ;Acyclic Monoterpenes ;Biochemistry ;Terpenes ;Aliphatics ;Chiral Reagents

(-)-beta-Citronellol Safety Profile

Safty information about 6-Octen-1-ol, 3,7-dimethyl-, (3S)- (CAS NO.7540-51-4) is:
Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 2
F: 8-10

(-)-beta-Citronellol Specification

6-Octen-1-ol, 3,7-dimethyl-, (3S)- , its cas register number is 7540-51-4. It also can be called AI3-09552 ; EINECS 231-415-7 ; FEMA No. 2309 ; beta-Citronellol ; l-Citronellol ; (-)-3,7-Dimethyloct-6-en-1-ol ; 6-Octen-1-ol, 3,7-dimethyl-, (S)- .It is a clear colorless liquid.

Product Name

BETA-RHODINOL

Synthetic route

(-)-beta-Citronellol Chemical Properties

(-)-beta-Citronellol Safety Profile

(-)-beta-Citronellol Specification

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