126-90-9

Basic information

• Product Name: (S)-3,7-dimethyl-1,6-octadien-3-ol
• Synonyms: (S)-3,7-dimethyl-1,6-octadien-3-ol;1,6-Octadien-3-ol, 3,7-dimethyl-, (3S)-;LINALOOLSYNTHETIC;(s)-3,7-dimethyl-1,6;6-Octadien-3-ol, 3,7-dimethyl-, (S)-1;7-dimethyl-6-octadien-3-o (s)-3;NATURAL Linalool;(S)-linalool
• CAS NO: 126-90-9
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.24932
• EINECS: 204-810-7
• Mol File: 126-90-9.mol
• Article Data: 29

Chemical Properties

• Melting Point: 38-39 °C
• Boiling Point: 198.5 °C at 760 mmHg
• Flash Point: 84.9 °C
• Appearance: /
• Density: 0.858 g/cm³
• Vapor Pressure: 0.0905mmHg at 25°C
• Refractive Index: 1.463
• PKA: 14.51±0.29(Predicted)
• CAS DataBase Reference: (S)-3,7-dimethyl-1,6-octadien-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3,7-dimethyl-1,6-octadien-3-ol(126-90-9)
• EPA Substance Registry System: (S)-3,7-dimethyl-1,6-octadien-3-ol(126-90-9)

Safety Data

• Hazardous Substances Data: 126-90-9(Hazardous Substances Data)

Usage

Definition

ChEBI: The (S)-enantiomer of linalool.

InChI:InChI=1/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3/t10-/m1/s1

Synthetic route

3,7-dimethyloct-6-en-1-yn-3-ol (29171-20-8) → 3,7-dimethyloct-6-en-3-ol (57029-98-8) + (S)-(+)-linalool (126-90-9)

Conditions	Yield
With hydrogen In hexane at 50℃; under 760.051 Torr; for 10h;	A 1% B 99%

Toluene-4-sulfonic acid <3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl>methyl ester (121401-06-7) → linalool (126-91-0) + (S)-(+)-linalool (126-90-9)

Conditions	Yield
With sodium hydroxide; tellurium; rongalite In tetrahydrofuran; water at 50 - 55℃; for 3h; Title compound not separated from byproducts;	A n/a B 97%
With sodium hydroxide; tellurium; sodium formaldehyde sulfoxylate In tetrahydrofuran for 2h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

3,7-dimethyl-octa-1,6-diene-3-ol-3-O-β-D-glucopyranoside (104154-37-2) → (S)-(+)-linalool (126-90-9)

Conditions	Yield
With Na2HPO4-citric buffer; β-D-glycosidase at 37℃; for 90h;	88%
With Na2HPO4-citrate buffer; β-glucosidase In water at 37℃; for 90h; pH=4.0; Hydrolysis;	88.2%

(S)-Benzyl linalyl ether (138052-31-0) → (S)-(+)-linalool (126-90-9)

Conditions	Yield
With ammonia; sodium In diethyl ether at -78℃; for 0.5h;	88%

(S)-6-Methyl-2-(S)-thiiranyl-hept-5-en-2-ol (160805-58-3) → (S)-(+)-linalool (126-90-9)

Conditions	Yield
With triethyl borane; tri-n-butyl-tin hydride In toluene at 0℃; for 0.0833333h;	84%

(2S,3R)-3-(bromomethyl)-2-methyl-2-(4-methylpent-3-en-1-yl)oxirane (91423-24-4) → linalool (126-91-0) + (S)-(+)-linalool (126-90-9)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -25℃; for 0.5h; Ring cleavage;	A n/a B 83%

Toluene-4-sulfonic acid <3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl>methyl ester (121401-06-7) → (S)-(+)-linalool (126-90-9)

Conditions	Yield
With zinc copper; sodium iodide In tetrahydrofuran for 2h; Heating;	78%
With sodium hydroxide; tellurium; rongalite In tetrahydrofuran; water at 50 - 55℃; for 3h; Product distribution; further reagent ratios, temperature, reagent, reaction times;

(2S,3S)-2,3-epoxygeraniol (82188-73-6) → (S)-(+)-linalool (126-90-9)

Conditions	Yield
With 1H-imidazole; 2,6-dimethylpyridine; water; iodine; triphenylphosphine In 1,2-dichloro-ethane; benzene at 75 - 80℃; for 2h; Mechanism; stereospecific 1,3-transposition of various chiral 2,3-epoxy alcohols;	77%
With 1H-imidazole; 2,6-dimethylpyridine; water; iodine; triphenylphosphine In 1,2-dichloro-ethane; benzene at 75 - 80℃; for 2h;	77%
Multi-step reaction with 2 steps 1: 84 percent / CBr4; triphenylphosphine / CH2Cl2 / 0 °C 2: 83 percent / BuLi / hexane; tetrahydrofuran / 0.5 h / -25 °C View Scheme

Toluene-4-sulfonic acid (2R,3S)-3-methyl-3-(4-methyl-pent-3-enyl)-oxiranylmethyl ester (166941-41-9) → (S)-(+)-linalool (126-90-9)

Conditions	Yield
With sodium hydroxide; tellurium; water; rongalite In tetrahydrofuran for 1h;	66%

(S)-5-Benzenesulfonyl-3,7-dimethyl-octa-1,6-dien-3-ol (52449-21-5, 86777-84-6, 86777-89-1, 86832-98-6, 102628-66-0, 102628-67-1) → (S)-(+)-linalool (126-90-9) + (E)-(S)-3,7-Dimethyl-octa-1,5-dien-3-ol (102628-68-2)

Conditions	Yield
With disodium hydrogenphosphate; sodium amalgam In methanol at 25℃; for 2.5h;	A 65% B n/a

(2S,3S)-2,3-epoxygeraniol (82188-73-6) → (S)-(+)-linalool (126-90-9) + (2S,3R)-1,3-Diiodo-3,7-dimethyl-oct-6-en-2-ol + (2S,3S)-3-Iodomethyl-2-methyl-2-(4-methyl-pent-3-enyl)-oxirane

Conditions	Yield
With 1H-imidazole; iodine; triphenylphosphine In benzene at 75 - 80℃; for 4h; Product distribution; stereospecific 1,3-transposition of various chiral 2,3-epoxy alcohols;	A 5% B 5% C 61%

(2S,3S)-3-Iodomethyl-2-methyl-2-(4-methyl-pent-3-enyl)-oxirane → (S)-(+)-linalool (126-90-9) + (2S,3R)-1,3-Diiodo-3,7-dimethyl-oct-6-en-2-ol

Conditions	Yield
With Ph3P(OH)I In 1,2-dichloro-ethane; benzene at 70 - 80℃; for 1h;	A 55% B 40%

3,7-dimethylocta-1,6-dien-3-ol (78-70-6) → (S)-(+)-linalool (126-90-9)

Conditions	Yield
durch linalylesterphthalsaeures Strychnin;

Geraniol (106-24-1) → terpineol (98-55-5) + (S)-(+)-linalool (126-90-9)

Conditions	Yield
iron(II) sulfate In toluene at 50℃; for 2h; Yield given. Yields of byproduct given;
zirconium(IV) sulfate In toluene at 50℃; for 1h; Yield given. Yields of byproduct given;

Toluene-4-sulfonic acid (2R,3R)-3-methyl-3-(4-methyl-pent-3-enyl)-oxiranylmethyl ester (121468-44-8) → linalool (126-91-0) + (S)-(+)-linalool (126-90-9)

Conditions	Yield
With sodium hydroxide; tellurium; sodium formaldehyde sulfoxylate In tetrahydrofuran for 5h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

4-(geranylseleno)-15-(p-toluenesulfonyl)<2.2>paracyclophane (135562-18-4, 135637-16-0) → 3,7-dimethylocta-1,6-dien-3-ol (78-70-6) + (S)-(+)-linalool (126-90-9)

Conditions	Yield
With triethylamine; 3-chloro-benzenecarboperoxoic acid Product distribution; 1) CH2Cl2, -66 deg C to -40 deg C, 10 min, 2) -40 deg to room temperature; stereoselectivity;

3(S)-Linalool β-D-(6'-O-β-L-Fucopyranosyl)glucopyranosid (84534-33-8, 104154-34-9, 131348-52-2, 131348-59-9) → D-glucose (50-99-7) + (S)-(+)-linalool (126-90-9) + 1-deoxy-L-galactitol (5328-43-8)

Conditions	Yield
With citrate buffer at 40℃; for 5h; enzyme hesperidinase;

3,7-dimethyl-octa-1,6-diene-3-ol-3-O-β-D-glucopyranoside (104154-37-2) → D-glucose (50-99-7) + (S)-(+)-linalool (126-90-9)

Conditions	Yield
With citrate buffer at 40℃; for 6h; enzyme hesperidinase;

linalyl glucoside → (S)-(+)-linalool (126-90-9)

Conditions	Yield
With cellulase (Sigma type II) In water Ambient temperature;	23 mg

trans-geranyl bromide (6138-90-5) → linalool (126-91-0) + (S)-(+)-linalool (126-90-9)

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

(3S)-linaloyl β-D-xylopyranosyl-(1->6)-β-D-glucopyranoside (158412-24-9) → 1-O-β-D-xylopyranosyl-(1,6)-β-D-glucopyranoside (133962-98-8) + (S)-(+)-linalool (126-90-9)

Conditions	Yield
With water at 37℃; for 1.5h; pH 6.0; hydrolysis by glucosidases II from tea leaves (cv. Yabukita); hydrolysis rate 63.0percent; further glucosidases and acetone powder from tea leaves;

(1S,2R,4R)-1-((E)-3,7-Dimethyl-octa-2,6-dienylselanylmethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol → linalool (126-91-0) + (S)-(+)-linalool (126-90-9)

Conditions	Yield
With tert-butylhypochlorite; sodium hydrogencarbonate Product distribution; multistep reaction;

(2R,3R)-3-methyl-3-(4-methyl-3-pentenyl)oxiranemethanol (50727-94-1, 62777-72-4, 62960-04-7, 71030-55-2, 76985-26-7, 82188-73-6, 112456-40-3, 112456-65-2, 62777-71-3) → linalool (126-91-0) + (S)-(+)-linalool (126-90-9)

Conditions	Yield
With 1H-imidazole; 2,6-dimethylpyridine; water; iodine; triphenylphosphine In 1,2-dichloro-ethane; benzene at 75 - 80℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

(2S,3R)-3,7-dimethyl-2,3-epoxy-6-octen-1-ol (76985-26-7) → linalool (126-91-0) + (S)-(+)-linalool (126-90-9)

Conditions	Yield
With 1H-imidazole; 2,6-dimethylpyridine; water; iodine; triphenylphosphine In 1,2-dichloro-ethane; benzene at 75 - 80℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

(S)-1-[2-((E)-3,7-Dimethyl-octa-2,6-dienylselanyl)-benzyl]-2-methoxymethyl-pyrrolidine → linalool (126-91-0) + (S)-(+)-linalool (126-90-9)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In diethyl ether at -90℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

linaloxymethyl butanoate (216861-19-7) → linalool (126-91-0) + butyl butyrate (109-21-7) + (S)-(+)-linalool (126-90-9)

Conditions	Yield
With pseudomonas fluorescens lipase; butan-1-ol In octane for 48h; Yield given;
With Candida rugosa lipase; butan-1-ol In octane at 45℃; for 4.25h; Yield given;

linaloxymethyl butanoate (216861-19-7) + butan-1-ol (71-36-3) → linalool (126-91-0) + butyl butyrate (109-21-7) + (S)-(+)-linalool (126-90-9)

Conditions	Yield
With Candida rugosa lipase In octane at 45℃; for 4.25h;
With Candida rugosa lipase In octane at 45℃; for 4.25h; Product distribution; various enzymes, solvents and temp.;

(2S,3R)-3-Iodomethyl-2-methyl-2-(4-methyl-pent-3-enyl)-oxirane (91423-25-5) → (S)-(+)-linalool (126-90-9)

Conditions	Yield
With water In diethyl ether; acetonitrile at 38℃; for 10h; reductive elimination;

(3S)-O-α-L-Rhamnopyranosyl-(1->3)-[4-O-(E)-coumaroyl]-α-L-rhamnopyranosyl-(1->6)-β-D-glucopyranosyllinalool → (S)-(+)-linalool (126-90-9)

Conditions	Yield
With hydrogenchloride at 20℃;	4.6 mg

Geraniol (106-24-1) → (S)-(+)-linalool (126-90-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 89 percent / 3 Angstroem sieves; 3 M t-butylhydroperoxide; (+)-diethyl tartrate / titanium(IV) isopropoxide / 2,2,4-trimethyl-pentane; CH2Cl2 / 0.75 h / -25 °C 2: 84 percent / CBr4; triphenylphosphine / CH2Cl2 / 0 °C 3: 83 percent / BuLi / hexane; tetrahydrofuran / 0.5 h / -25 °C View Scheme
Multi-step reaction with 2 steps 2: 78 percent / zinc-copper couple, NaI / tetrahydrofuran / 2 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 91 percent / (+)-DIPT,m Ti(OiPr)4, t-BuOOH, molecular sieves 4 Angstroem / CH2Cl2 / -34 °C 2: 94 percent / NEt3, 4-dimethylaminopyridine / CH2Cl2 / -10 °C 3: Te-rongalite, aq. NaOH / tetrahydrofuran / 2 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 85 percent / (-)-DIPT, Ti(OiPr)4, t-BuOOH, molecular sieves 4 Angstroem / CH2Cl2 / -34 °C 2: 86 percent / NEt3, 4-dimethylaminopyridine / CH2Cl2 / -10 °C 3: Te-rongalite, aq. NaOH / tetrahydrofuran / 5 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 91 percent / tert-BuOOH (TBHP), (+)-diisopropyl tartrate, Ti(O-i-Pr)4 / CH2Cl2 / -37 °C 2: Et3N, dimethylaminopyridine (DMAP) / CH2Cl2 / 15 h / -10 °C 3: 66 percent / tellurium, HOCH2SO2Na, NaOH, H2O / tetrahydrofuran / 1 h View Scheme

(S)-(+)-linalool (126-90-9) → 3,7-dimethyloct-6-en-3-ol (57029-98-8)

Conditions	Yield
With oxygen; 5-ethyl-10-methyl-2,4-dioxo-2,3,4,10-tetrahydrobenzo[g]pteridin-5-ium perchlorate; hydrazine hydrate In acetonitrile at 25℃; under 760 Torr; for 5h;	96%
With hydrazine hydrate In chloroform at 25℃; under 760.051 Torr; for 24h; Reagent/catalyst;	79 %Chromat.

triethylsilyl chloride (994-30-9) + (S)-(+)-linalool (126-90-9) → (S)-((3,7-dimethylocta-1,6-dien-3-yl)oxy)triethylsilane

Conditions	Yield
With 1,2,2,6,6-pentamethylpiperidine; 1-methyl-1H-imidazole-3-oxide In chloroform at 40℃; for 8h; Inert atmosphere;	95%

t-butyldimethylsiyl triflate (69739-34-0) + (S)-(+)-linalool (126-90-9) → (S)-tert-butyl((3,7-dimethylocta-1,6-dien-3-yl)oxy)dimethylsilane

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;	90%

(S)-(+)-linalool (126-90-9) → (2RS,5S)-2-hydroxy-5-methyl-5-vinyltetrahydrofuran (35468-92-9, 35469-30-8, 40478-73-7)

Conditions	Yield
With pyridine; ozone In dichloromethane at -78℃; for 0.75h;	88%

(S)-(+)-linalool (126-90-9) → (R)-5-(1-Bromo-1-methyl-ethyl)-2-methyl-2-vinyl-tetrahydro-furan

Conditions	Yield
With N-Bromosuccinimide In dichloromethane for 48h; Ambient temperature;	85%

(S)-(+)-linalool (126-90-9) → (S)-2-methyl-1,2,5-pentanetriol (57624-95-0)

Conditions	Yield
Stage #1: (S)-(+)-linalool With ozone In methanol; dichloromethane at -78℃; for 0.0833333h; Stage #2: With sodium tetrahydroborate In methanol; dichloromethane at 0℃; Further stages.;	77%

acetic anhydride (108-24-7) + (S)-(+)-linalool (126-90-9) → (S)-linalyl acetate (115-95-7, 16509-46-9, 40135-38-4, 51685-40-6)

Conditions	Yield
With dmap; triethylamine at 20℃; for 10h; Acetylation;	70%
With pyridine; dmap at 90℃; for 44h; Acetylation;

(S)-(+)-linalool (126-90-9) → (1S,2R,5S)-(+)-2,6,6-trimethylbicyclo<3.2.0>heptan-endo-2-ol (132957-45-0)

Conditions	Yield
With silver hexafluoroantimonate; di-μ-chloro-bis(1,5-cyclooctadiene)dicopper In diethyl ether at 20℃; for 5h; Reagent/catalyst; Inert atmosphere; UV-irradiation;	68%

(S)-(+)-linalool (126-90-9) + 2,3,4-tri-O-acetyl-6-O-<(3-C-acetoxymethyl)-2,3-di-O-acetyl-β-D-erythrofuranosyl>-α-D-glucopyranosyl trichloroacetimidate → (3S)-linalyl 2,3,4-tri-O-acetyl-6-O-<(3-C-acetoxymethyl)-2,3-di-O-acetyl-β-D-erythrofuranosyl>-β-D-glucopyranoside (156058-58-1)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane Ambient temperature;	62%

Phenylselenyl chloride (5707-04-0) + (S)-(+)-linalool (126-90-9) → (R)-2-Methyl-5-(1-methyl-1-phenylselanyl-ethyl)-2-vinyl-tetrahydro-furan

Conditions	Yield
In dichloromethane for 12h; Ambient temperature;	45%

(S)-(+)-linalool (126-90-9) → 5-bromo-2,6,6-trimethyl-(5R)-tetrahydropyran-2-carbaldehyde (240133-55-5) + 5-bromo-2,6,6-trimethyl-(5S)-tetrahydropyran-2-carbaldehyde

Conditions	Yield
Stage #1: (S)-(+)-linalool With 2,2,4,6-tetrabromocyclohexa-2,5-dienone In nitromethane at 0℃; for 5h; Stage #2: With osmium(VIII) oxide; N-methyl-2-indolinone In tetrahydrofuran at 20℃; for 24h; Stage #3: With sodium periodate In tetrahydrofuran at 0 - 20℃; Further stages.;	A 13% B 25%

(S)-(+)-linalool (126-90-9) → geranyl chloride (4490-10-2)

Conditions	Yield
With pyridine; thionyl chloride
With Petroleum ether; phosphorus trichloride unter Kuehlung;
Multi-step reaction with 3 steps 1: toluene; HBr 2: AgNO3 3: K2CO3; benzene; PCl3 / 0 - 5 °C View Scheme

(S)-(+)-linalool (126-90-9) → geranyl chloride (4490-10-2) + (R)-3-chloro-3,7-dimethyl-octa-1,6-diene (471-10-3)

Conditions	Yield
With phosphorus trichloride
With phosphorus trichloride

(S)-(+)-linalool (126-90-9) → geranyl bromide (6138-90-5)

Conditions	Yield
With hydrogen bromide; toluene

(S)-(+)-linalool (126-90-9) → terpineol (98-55-5)

Conditions	Yield
With formic acid l-α-terpineol;

(S)-(+)-linalool (126-90-9) → limonene. (138-86-3)

Conditions	Yield
With on fired clay applied aluminium oxide at 310℃; dl-limonene;

(S)-(+)-linalool (126-90-9) + phenyl isocyanate (103-71-9) → phenylcarbamic acid-((R)-linalyl ester); carbanilic acid ester of d-linalool (93477-63-5, 118723-77-6)

Conditions	Yield

Upstream product

• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 106-24-1 Geraniol 
• 158412-24-9 (3S)-linaloyl β-D-xylopyranosyl-(1->6)-β-D-glucopyranoside 
• 104154-37-2 3,7-dimethyl-octa-1,6-diene-3-ol-3-O-β-D-glucopyranoside 
• 82188-73-6 (2S,3S)-2,3-epoxygeraniol 
• 50727-94-1 (2R,3R)-3-methyl-3-(4-methyl-3-pentenyl)oxiranemethanol 
• 76985-26-7 (2S,3R)-3,7-dimethyl-2,3-epoxy-6-octen-1-ol 
• 216861-19-7 linaloxymethyl butanoate 
• 71-36-3 butan-1-ol 
• 91423-24-4 (2S,3R)-3-(bromomethyl)-2-methyl-2-(4-methylpent-3-en-1-yl)oxirane 
• 62777-72-4 (2R,3S)-2,3-epoxynerol 
• 61573-90-8 ((2S,3S)-3-methyl-3-(4-methylpent-3-en-1-yl)oxiran-2-yl)methyl methanesulfonate 
• 137958-62-4 (2S,3S)-3-Benzyloxy-1,2-diacetoxy-3,7-dimethyl-6-octene 
• 137958-61-3 (2S,3S)-3-Benzyloxy-3,7-dimethyl-oct-6-ene-1,2-diol 

Downstream Products

• 4490-10-2 geranyl chloride 
• 471-10-3 (R)-3-chloro-3,7-dimethyl-octa-1,6-diene 
• 6138-90-5 geranyl bromide 
• 98-55-5 terpineol 
• 138-86-3 limonene. 
• 56577-25-4 (R)-3,7-dimethyl-3-octanol 
• 464-45-9 endo-borneol 
• 2451-01-6 cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate 
• 10482-56-1 (-)-(S)-α-terpineol 
• 57029-98-8 3,7-dimethyloct-6-en-3-ol 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 22882-91-3 3,7-dimethyl-(2E)-2,6-octadienyl ethyl ether 
• 72845-33-1 3-(1-ethoxy)-3,7-dimethyl-1,6-octadiene 
• 240133-67-9 3-((2S,3R,6R)-6-Benzyloxymethyl-2-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-yl)-1-((2S,5R)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-propynone 

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Transcriptome profiling, and cloning and characterization of the main monoterpene synthases of Coriandrum sativum L.

Terpenoids are a large and diverse class of specialized metabolites that are essential for the growth and development of plants, and have tremendous industrial applications. The mericarps of Coriandrum sativum L. (coriander) produce an essential oil (EO) rich in monoterpenes, volatile C10 terpenoids. To investigate EO metabolism, the transcriptome of coriander mericarps, at three developmental stages (early, mid, late) was sequenced via Illumina technology and a transcript library was produced. To validate the usability of the transcriptome sequences, two terpene synthase candidate genes, CsγTRPS and CsLINS, encoding 558 and 562 amino acid proteins were expressed in bacteria, and the recombinant proteins purified by Ni-NTA affinity chromatography. The 65.16 (CsγTRPS) and 65.91 (CsLINS) kDa recombinant proteins catalyzed the conversion of geranyl diphosphate, the precursor to monoterpenes, to γ-terpinene and (S)-linalool, respectively, with apparent Vmax and Km values of 2.24 ± 0.16 (CsγTRPS); 19.63 ± 1.05 (CsLINS) pkat/mg and 66.25 ± 13 (CsγTRPS); 2.5 ± 0.6 (CsLINS) μM, respectively. Together, CsγTRPS and CsLINS account for the majority of EO constituents in coriander mericarps. Investigation of the coriander transcriptome, and knowledge gained from these experiments will facilitate future studies concerning essential and fatty acid oil production in coriander. They also enable efforts to improve the coriander oils through metabolic engineering or plant breeding.

Synthesis and reactions of the optically active selenols derived from monoterpenes Dedicated to Professor Jacek Gawronski on the occasion of his 70th birthday

A convenient methodology for the synthesis of optically active selenols, derived from p-menthane, carane, and pinane, is described. The selenols were oxidized with air to give the optically active diselenides, and were also converted into the corresponding allylic selenides via reaction with Z- and E-cinnamyl, geranyl, and neryl chlorides. Oxidation of the allylic selenides with mCPBA gave the optically active alcohols via [2,3]-sigmatropic rearrangement of the in situ generated allylic selenoxides.