78-69-3

Basic information

• Product Name: Tetrahydrolinalool
• Synonyms: TETRAHYDROLINALOOL;3-OCTANOL, 3,7-DIMETHYL;3,7-DIMETHYL-3-OCTANOL;FEMA 3060;(±)-3,7-dimethyl-octan-3-ol;2,6-Dimethyl-6-octanol;3,7-dimethyl-3-octano;3,7-Dimethyloctan-3-ol
• CAS NO: 78-69-3
• Molecular Formula: C₁₀H₂₂O
• Molecular Weight: 158.28
• EINECS: 201-133-9
• Product Categories: Alphabetical Listings;Flavors and Fragrances;Q-Z
• Mol File: 78-69-3.mol
• Article Data: 22

Chemical Properties

• Melting Point: -1.53°C (estimate)
• Boiling Point: 71-73 °C6 mm Hg(lit.)
• Flash Point: 169 °F
• Appearance: Clear colorless/Liquid
• Density: 0.826 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.115mmHg at 25°C
• Refractive Index: n20/D 1.434(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 15.34±0.29(Predicted)
• Water Solubility: 320mg/L at 25℃
• CAS DataBase Reference: Tetrahydrolinalool(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrahydrolinalool(78-69-3)
• EPA Substance Registry System: Tetrahydrolinalool(78-69-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36/38
• Safety Statements: 26-36-37/39
• RIDADR: NA 1993 / PGIII
• WGK Germany: 1
• RTECS: RH0905000
• Hazardous Substances Data: 78-69-3(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 78-69-3 differently. You can refer to the following data:
1. Tetrahydrolinalool is a constituent of honey aroma. It is a colorless liquid with a linalool-like odor that is slightly fresher but distinctly weaker than that of linalool. Tetrahydrolinalool is prepared by catalytic hydrogenation of linalool and is used as a substitute for the less stable linalool in perfuming aggressive media.
2. Tetrahydrolinalool has a sweet, oily, floral odor (more so than linalool) with a citrus floral taste.
3. Clear colorless liquid

Occurrence

Reported found in Virginia tobacco.

Uses

Perfumery, flavoring.

Preparation

By hydrogenation of dl-linalool in the presence of palladium black according to Barbier and Lacquin; also from magnesium ethyl bromide and isoamylketone, or by hydrogenation of 2,6-dimethyl-2-octen-6-ol in the presence of nickel at 100°C; optically active and racemic forms are expected because of the structure of this product.

Definition

ChEBI: A fatty alcohol that is 3-octanol substituted by methyl groups at positions 3 and 7. Metabolite observed in cancer metabolism.

Aroma threshold values

Aroma characteristics at 1%: floral linalool-like with a fatty citrus rind and tea-like nuance.

Taste threshold values

Taste characteristics at 1 to 15 ppm: clean and fresh, floral, tea-like with citrus and herbal nuances.

General Description

The chlorooxidation of 3,7-dimethyl-3-octanol (tetrahydrolinalool) was studied.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C10H22O/c1-5-10(4,11)8-6-7-9(2)3/h9,11H,5-8H2,1-4H3/t10-/m0/s1

Synthetic route

2,6-dimethyl-6-(triphenylsilyloxy)octane → tetrahydrolinalool (78-69-3)

Conditions	Yield
With naphthalene; lithium In tetrahydrofuran; methanol at 20℃; for 5h;	98%

6-Methoxymethoxy-2,6-dimethyl-octane (144708-84-9) → tetrahydrolinalool (78-69-3)

Conditions	Yield
With methanol; DOWEX-50W-X2 for 2h; Heating;	94%

3,7-dimethylocta-1,6-dien-3-ol (78-70-6) → tetrahydrolinalool (78-69-3)

Conditions	Yield
With ammonium chloride In methanol Electrochemical reaction;	93%
With (bis-1,2-diphenylphosphinoethane)Co(CH2SiMe3)2; hydrogen In toluene at -196.15 - 25℃; under 3040.2 Torr; for 14h; Reagent/catalyst; Sealed tube;	82%
With hydrogen at 80℃; under 7500.75 Torr; for 1h; Autoclave;	68%

3,7-dimethylocta-1,6-dien-3-ol (78-70-6) → tetrahydrolinalool (78-69-3) + dihydrolinalool (18479-51-1)

Conditions	Yield
With iron(III) chloride hexahydrate; hydrazine hydrate In ethanol at 80℃; for 36h;	A 82% B 18%
With air; hydrazine hydrate In ethanol at 25℃; for 4h;

linalool (126-91-0) → tetrahydrolinalool (78-69-3)

Conditions	Yield
With hydrogen; platinum levorotatory substances of 2,6-dimethyl-octanol-(6);
With ethanol; water; hydrogen in Gegenwart von Katalysatoren der Platingruppe; levorotatory substances of 2,6-dimethyl-octanol-(6);

3,7-dimethylocta-1,6-dien-3-ol (78-70-6) → 2,6-dimethyloctane (2051-30-1) + tetrahydrolinalool (78-69-3)

Conditions	Yield
With hydrogen; nickel at 130 - 140℃; Hydrogenation;
With hydrogen; nickel

3-methyl-1-butyl acetate (123-92-2) + ethylmagnesium bromide (925-90-6) → tetrahydrolinalool (78-69-3)

Conditions	Yield
inactive form of 2,6-dimethyl-octanol-(6);

dihydrolinalool (18479-51-1) → 2,6-dimethyloctane (2051-30-1) + tetrahydrolinalool (78-69-3)

Conditions	Yield
With hydrogen; nickel at 130 - 140℃; Hydrogenation;
With hydrogen; nickel

dihydrolinalool (18479-51-1) → tetrahydrolinalool (78-69-3)

Conditions	Yield
With nickel pumice stone at 100℃; under 15 Torr; Hydrogenation;

hydrodehydrolinalool (1604-26-8) → tetrahydrolinalool (78-69-3)

Conditions	Yield
With platinum Hydrogenation;
With nickel Hydrogenation;

(S)-2-ethyl-6-methyl-heptylamine (33204-58-9) → tetrahydrolinalool (78-69-3)

Conditions	Yield
With perchloric acid; sodium nitrite

(5Ξ,6S)-2,6-dimethyl-5-(toluene-4-sulfonyloxy)-octane (34038-41-0) → tetrahydrolinalool (78-69-3)

Conditions	Yield
With sodium acetate In 1,4-dioxane

2,6-dimethyloctane (2051-30-1) → tetrahydrolinalool (78-69-3) + 2,6-dimethyl-2-octanol (18479-57-7)

Conditions	Yield
With 4-nitroperbenzoic acid In chloroform at 60℃; Rate constant; proportion of velocity of the hydroxylation of tert- and sec. C-H-bonds;
With 4-nitroperbenzoic acid In chloroform at 60℃; Yield given. Yields of byproduct given;
With potassium fluoride; perfluoro-cis-2-n-butyl-3-n-propyloxaziridine In trichlorofluoromethane at 20℃; Product distribution; Further Variations:; Reagents; time;

3,7-dimethyloct-6-en-1-yn-3-ol (29171-20-8) → 3,7-dimethylocta-1,6-dien-3-ol (78-70-6) + tetrahydrolinalool (78-69-3)

Conditions	Yield
With hydrogen; modified (Zn(CH3COO)2+pyridine+KOH) ShPAK-0.5 (0.5percent Pd/Al2O3) In methanol at 55℃; p(H2)=0.04 MPa;
With hydrogen; ShPAK-0.5 (0.5percent Pd/Al2O3) In methanol at 55℃; Product distribution; var. temp. and p(H2), Zn(CH3COO)2 and pyridine+KOH modified catalysts; apparent activation energies;
With hydrogen; ShPAK-0.5 modified by Zn(OAc)2 + NH3 at 65℃; under 7355.08 - 11768.1 Torr; for 3.5h;

dihydrolinalool → tetrahydrolinalool (78-69-3)

Conditions	Yield
With ethanol; water; hydrogen in Gegenwart von Katalysatoren der Platingruppe; levorotatory substances of 2,6-dimethyl-octanol-(6);

3,7-dimethyl-oct-7-en-3-ol (18479-52-2) + nickel pumice stone → tetrahydrolinalool (78-69-3)

Conditions	Yield
at 100℃; under 15 Torr; Hydrogenation;

ethanol (64-17-5) + linalool (126-91-0) + palladium + hydrogen → tetrahydrolinalool (78-69-3)

Conditions	Yield
mit mehr Wasserstoff;

hydrodehydrolinalool (1604-26-8) + hydrogen + platinum black → tetrahydrolinalool (78-69-3)

Conditions	Yield
bei gewoehnlichem Druck;

ethanol (64-17-5) + linalool (126-91-0) + platinum → tetrahydrolinalool (78-69-3)

Conditions	Yield
Hydrogenation;

ethanol (64-17-5) + linalool (126-91-0) + platinum + hydrogen → tetrahydrolinalool (78-69-3)

Conditions	Yield
mit mehr Wasserstoff;

(R)-3,7-dimethyl-3-octanol (56577-25-4) + sulfuric acid (7664-93-9) → 3,7-dimethyl-oct-3-ene (56523-31-0) + 3,7-dimethyl-oct-2-ene (6874-06-2, 6874-32-4, 56523-30-9) + tetrahydrolinalool (78-69-3)

Conditions	Yield
at 100℃;

linalool (126-91-0) + hydrogen + copper → 2,6-dimethyloctane (2051-30-1) + tetrahydrolinalool (78-69-3)

Conditions	Yield
Hydrogenation;

linalool (126-91-0) + hydrogen + nickel → 2,6-dimethyloctane (2051-30-1) + tetrahydrolinalool (78-69-3)

Conditions	Yield
Hydrogenation;

dihydrolinalool (18479-51-1) + nickel + hydrogen → 2,6-dimethyloctane (2051-30-1) + tetrahydrolinalool (78-69-3)

Conditions	Yield
Hydrogenation;

(+-)-3,7-dimethyl-oct-1-en-3-ol → tetrahydrolinalool (78-69-3)

Conditions	Yield
With methanol; platinum Hydrogenation;

(R)-3,7-dimethyl-3-octanol (56577-25-4) → tetrahydrolinalool (78-69-3) + 2.6-dimethyl-octen-(6) and 2.6-dimethyl-octene-(5)

Conditions	Yield
With sulfuric acid at 100℃;

benzyl 3,7-dimethyl-3-octyl carbonate → tetrahydrolinalool (78-69-3)

Conditions	Yield
With naphthalen-1-yl-lithium In tetrahydrofuran at 0℃; for 5h;	81 % Chromat.

3,7-dimethyl-3-octyl pivalate → tetrahydrolinalool (78-69-3)

Conditions	Yield
With naphthalene; lithium In tetrahydrofuran at 0℃; for 4h;	38 % Chromat.

tetrahydrolinalool (78-69-3) → 3-bromo-3,7-dimethyloctane (1142814-79-6)

Conditions	Yield
With trimethylsilyl bromide In neat (no solvent) at 20℃; for 15h; Inert atmosphere;	94%
With phosphorus tribromide

tetrahydrolinalool (78-69-3) + t-butoxalyl chloride (39061-59-1) → tert-butyl (3,7-dimethyloctan-3-yl) oxalate

Conditions	Yield
With pyridine; dmap In dichloromethane at 0 - 20℃; Inert atmosphere;	94%

tetrahydrolinalool (78-69-3) + diethyl(isopropyl)silyl trifluoromethanesulfonate (126889-55-2) → Diethyl-(1-ethyl-1,5-dimethyl-hexyloxy)-isopropyl-silane (126909-57-7)

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane Ambient temperature;	90%

tetrahydrolinalool (78-69-3) + benzyl chloroformate (501-53-1) → benzyl 3,7-dimethyl-3-octyl carbonate

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2h;	87%

tetrahydrolinalool (78-69-3) + ethyl acrylate (140-88-5) → ethyl 4-ethyl-4,8-dimethylnonanoate

Conditions	Yield
With cyclopentadienyl titanium(IV) trichloride; triethylsilyl chloride; zinc In tetrahydrofuran at 60℃; for 12h; Molecular sieve; Sealed tube; Inert atmosphere;	85%

tetrahydrolinalool (78-69-3) → 6-hydroperoxy-2,6-dimethyloctane

Conditions	Yield
With sulfuric acid; dihydrogen peroxide In 1,4-dioxane; water at -10 - 60℃;	83%

tetrahydrolinalool (78-69-3) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 3,7-dimethyl-3-trimethylsiloxyoctane

Conditions	Yield
With iodine In dichloromethane for 1h;	78%

tetrahydrolinalool (78-69-3) → 7-chloro-3,7-dimethyloctan-3-ol

Conditions	Yield
With dichloro(1,10-phenanthroline) copper(II); 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one In 1,2-dichloro-ethane at 50℃; for 48h; Inert atmosphere; Sealed tube;	78%

tetrahydrolinalool (78-69-3) + pivaloyl chloride (3282-30-2) → 3,7-dimethyl-3-octyl pivalate

Conditions	Yield
Stage #1: tetrahydrolinalool With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.166667h; Stage #2: pivaloyl chloride In tetrahydrofuran; hexane at 0℃; for 1h;	75%

tetrahydrolinalool (78-69-3) → 2,6-dimethyloctane-2,6-diol (54796-79-1)

Conditions	Yield
With 1,1,1,3',3',3'-hexafluoro-propanol; 3,4-dihydro-2,4,4-trimethyl-1-(trifluoromethyl)isoquinolinium tetrafluoroborate; dihydrogen peroxide In water at 20℃; for 20h; chemoselective reaction;	58%
With Oxone; 1,1,1-trifluoro-2-hexanone; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In water at 4℃; for 72h; Sealed tube;	34%
With 3,3-dimethyldioxirane In acetone for 24h; Ambient temperature;
With 3,3-dimethyldioxirane In acetone Rate constant; Ambient temperature; different solvents;
With iodosylbenzene; C40H39ClN4OPRu(1+)*Cl(1-); trifluoroacetic acid In 1,1,2,2-tetrachloroethane at 35℃; for 30h; regioselective reaction;

tetrahydrolinalool (78-69-3) + mono-L-menthyl glutarate (220621-22-7) → L-menthyl tetrahydrolinalyl glutarate

Conditions	Yield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20 - 35℃; for 69.5h; Cooling with ice;	49%

formic acid (64-18-6) + tetrahydrolinalool (78-69-3) → 3,7-dimethyl-oct-2-ene (6874-06-2, 6874-32-4, 56523-30-9)

Conditions	Yield
inactive form of 2,6-dimethyl-octanol-(6);
at 100℃; levorotatory substances of 2,6-dimethyl-octanol-(6);

tetrahydrolinalool (78-69-3) + (E)-3-Ureido-but-2-enoic acid ethyl ester (5435-44-9, 22243-66-9) → 3,7-dimethyl-oct-2-ene (6874-06-2, 6874-32-4, 56523-30-9)

Conditions	Yield
at 170℃; inactive form of 2,6-dimethyl-octanol-(6);

tetrahydrolinalool (78-69-3) → 3,7-dimethyl-oct-3-ene (56523-31-0) + 3,7-dimethyl-oct-2-ene (6874-06-2, 6874-32-4, 56523-30-9)

Conditions	Yield
With sulfuric acid at 100℃;

tetrahydrolinalool (78-69-3) → 3,7-dimethyl-oct-2-ene (6874-06-2, 6874-32-4, 56523-30-9)

Conditions	Yield
With zinc(II) chloride at 170℃;

tetrahydrolinalool (78-69-3) → 2,6-dimethyloctane (2051-30-1)

Conditions	Yield
With aluminum oxide Dehydratisieren und Hydrieren des Reaktionsprodukts;

tetrahydrolinalool (78-69-3) → 6-chloro-2,6-dimethyl-octane (54059-75-5)

tetrahydrolinalool (78-69-3) + 2-oxo-propionic acid (127-17-3) → 3,7-dimethyl-oct-2-ene (6874-06-2, 6874-32-4, 56523-30-9)

Conditions	Yield
at 140℃; levorotatory substances of 2,6-dimethyl-octanol-(6);

diazomethane (186581-53-3, 908094-01-9) + formaldehyd (50-00-0) + tetrahydrolinalool (78-69-3) → 2-Ethyl-2,6-dimethyl-heptanoic acid methyl ester (43010-58-8)

Conditions	Yield
(i) H2SO4, (ii) /BRN= 102415/; Multistep reaction;

Upstream product

• 126-91-0 linalool 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 29171-20-8 3,7-dimethyloct-6-en-1-yn-3-ol 
• 56577-25-4 (R)-3,7-dimethyl-3-octanol 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 1142814-79-6 3-bromo-3,7-dimethyloctane 
• 838835-60-2 trans-4-methyl-1-cyclohexyl pivalate 
• 928-68-7 6-methylheptan-2-one 
• 18479-51-1 dihydrolinalool 
• 7664-93-9 sulfuric acid 
• 64-17-5 ethanol 
• 1604-26-8 hydrodehydrolinalool 
• 18479-52-2 3,7-dimethyl-oct-7-en-3-ol 
• 144708-84-9 6-Methoxymethoxy-2,6-dimethyl-octane 

Downstream Products

• 67-64-1 acetone 
• 928-68-7 6-methylheptan-2-one 
• 78-93-3 butanone 
• 54059-75-5 Tetrahydrolinalychlorid 

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