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Citronellol

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Name

Citronellol

EINECS 203-375-0
CAS No. 106-22-9 Density 0.845 g/cm3
PSA 20.23000 LogP 2.75130
Solubility slightly soluble in water Melting Point 77-83 °C(lit.)
Formula C10H20O Boiling Point 224.499 °C at 760 mmHg
Molecular Weight 156.268 Flash Point 98.333 °C
Transport Information N/A Appearance colourless liquid
Safety 26-36-24/25 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 106-22-9 (6-Octen-1-ol,3,7-dimethyl-) Hazard Symbols IrritantXi
Synonyms

2,3-Dihydrogeraniol;2,6-Dimethyl-2-octen-8-ol;3,7-Dimethyl-6-octen-1-ol;Cephrol;Citronellol 950;Dihydrogeraniol;Rodinol;

Article Data 270

Citronellol Synthetic route

106-23-0, 26489-02-1

3,7-dimethyl-oct-6-enal

106-22-9

Citronellol

Conditions
ConditionsYield
With Zn(BH4)2(Ph3P)2 In tetrahydrofuran at 20℃; Reduction;100%
With hydrogen; aluminum oxide; copper In isopropyl alcohol at 90℃; for 0.75h;100%
With trimethylamine-N-oxide; sodium formate; C34H44FeN4O4(2+)*2I(1-) In water at 80℃; for 24h; Inert atmosphere; Schlenk technique;99%
106-24-1

Geraniol

106-22-9

Citronellol

Conditions
ConditionsYield
With hydrogen; aluminum oxide; copper In isopropyl alcohol at 90℃; for 12h;100%
With hydrogen; polymer-supported rhodium catalyst In dichloromethane under 1551.49 Torr; for 10h; Hydrogenation;96%
With 1,1'-bis(diphenylphosphino)ferrocene; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; Butane-1,4-diol; potassium tert-butylate at 110℃; for 24h; Inert atmosphere;71%
106-22-9

Citronellol

Conditions
ConditionsYield
With hydrogen; aluminum oxide; copper In isopropyl alcohol at 90℃; for 12h;100%
With dichloro(η3:η2:η3-dodeca-2,6,10-triene-1,12-diyl)ruthenium(IV); caesium carbonate; isopropyl alcohol at 82℃; for 23h; Inert atmosphere; chemoselective reaction;95 %Chromat.
96154-40-4

1-(benzyloxy)-3,7-dimethyloct-6-ene

106-22-9

Citronellol

Conditions
ConditionsYield
With hydrogen; benzyl bromide; Pd<*>MCM-48 In methanol under 760.051 Torr; for 0.5h;99%
With aluminium trichloride; N,N-dimethyl-aniline In dichloromethane for 1.5h; Ambient temperature;98%
With naphthalene; lithium In tetrahydrofuran; methanol at -78℃; for 40h;89%
2270-60-2

methyl 3,7-dimethyloct-6-enoate

106-22-9

Citronellol

Conditions
ConditionsYield
With [RuCl2((E)-N-(2-(diphenylphosphino)benzyl)-1-(6-((diphenylphosphino)methyl)pyridin-2-yl)methanimine)]; hydrogen; sodium ethanolate at 80℃; under 37503.8 Torr; for 5h; Autoclave;98%
With lithium aluminium tetrahydride Yield given;

1-(3,7-Dimethyl-oct-6-enyloxymethoxy)-4-methoxy-benzene

106-22-9

Citronellol

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In water; acetonitrile at 0℃; for 0.5h; Product distribution;98%
90243-41-7

2-(3,7-dimethyloct-6-enyloxy)-tetrahydro-2H-pyran

106-22-9

Citronellol

Conditions
ConditionsYield
With SA-3 silica-alumina gel In methanol at 120℃; for 2.16667h;98%
With SA-3 silica-alumina gel In methanol at 120℃; for 2.16667h; Product distribution; other ethers, var. silica-alumina gels, temp. and time;98%
With copper dichloride In methanol at 20℃; Hydrolysis;90%
With CuCl2*2H2O In methanol at 20℃; for 1.25h;90%
With boron trifluoride diethyl etherate; sodium cyanoborohydride In tetrahydrofuran for 3h; Ambient temperature;80%

Acetaldehyde ethyl 3,7-dimethyl-6-octenyl acetal

106-22-9

Citronellol

Conditions
ConditionsYield
With SA-3 silica-alumina gel In methanol at 120℃; for 1.33333h;98%

8-(1-Methoxy-ethoxy)-2,6-dimethyl-oct-2-ene

106-22-9

Citronellol

Conditions
ConditionsYield
With dibromotriphenylphosphorane In dichloromethane at -50℃; for 2h;97%
18419-09-5

(3,7-dimethyloct-6-enyloxy)trimethylsilane

106-22-9

Citronellol

Conditions
ConditionsYield
With SA-3 silica-alumina gel In methanol for 1.16667h; Ambient temperature;97%
With 18-crown-6 ether In ethanol; water at 45℃; for 3h; Green chemistry;91%

Citronellol Consensus Reports

Citronellol (106-22-9) is reported in EPA TSCA Inventory.

Citronellol Specification

The Citronellol, with the CAS registry number 106-22-9, is also known as 2,3-Dihydrogeraniol. It belongs to the product categories of Acyclic Monoterpenes; Biochemistry; Terpenes; Alphabetical Listings; C-D; Flavors and Fragrances; Acyclic; Alcohols; Alkenes; Building Blocks; C9 to C10; Chemical Synthesis; Organic Building Blocks; Oxygen Compounds. Its EINECS registry number is 203-375-0. This chemical's molecular formula is C10H20O and molecular weight is 156.27. What's more, both its IUPAC name and systematic name are the same which is called 3,7-Dimethyloct-6-en-1-ol. It should be stored in a cool, dry and well-ventilated place.

Physical properties about Citronellol are: (1)ACD/LogP: 3.382; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.38; (4)ACD/LogD (pH 7.4): 3.38; (5)ACD/BCF (pH 5.5): 218.92; (6)ACD/BCF (pH 7.4): 218.92; (7)ACD/KOC (pH 5.5): 1647.35; (8)ACD/KOC (pH 7.4): 1647.35; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 20.23 Å2; (13)Index of Refraction: 1.45; (14)Molar Refractivity: 49.772 cm3; (15)Molar Volume: 184.902 cm3; (16)Polarizability: 19.731×10-24cm3; (17)Surface Tension: 28.578 dyne/cm; (18)Density: 0.845 g/cm3; (19)Flash Point: 98.333 °C; (20)Enthalpy of Vaporization: 53.601 kJ/mol; (21)Boiling Point: 224.499 °C at 760 mmHg; (22)Vapour Pressure: 0.018 mmHg at 25 °C.

Preparation of Citronellol: this chemical can be prepared by 8-allyloxy-2,6-dimethyl-oct-2-ene. This reaction needs reagents Li, ROMP gel supported naphthalene and solvents tetrahydrofuran, methanol at temperature of -78 °C. The reaction time is 40 hours. The yield is 86 %.

Citronellol can be prepared by 8-allyloxy-2,6-dimethyl-oct-2-ene.

Uses of Citronellol: (1) it is can be used for the production of paint desiccant, dyeing mordant, glass and steel curing accelerator, and invisible ink and so on; (2) it is used to produce other chemicals. For example, it can react with propionic acid methyl ester to get (S)-citronellyl propionate. The reaction occurs with reagent 0.1 M phosphate buffer and other condition of ambient temperature for 96 hours. The yield is 58 %.

 Citronellol can react with propionic acid methyl ester to get (S)-citronellyl propionate.

When you are dealing with this chemical, you should be very careful. This chemical may cause inflammation to the skin or other mucous membranes. And it is irritating to eyes, respiratory system and skin. Therefore, you should wear suitable protective clothing and avoid contacting with skin and eyes. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: C\C(C)=C\CCC(C)CCO
(2) InChI: InChI=1S/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3
(3) InChIKey: QMVPMAAFGQKVCJ-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intramuscular 4gm/kg (4000mg/kg)   Journal of Scientific and Industrial Research, Section C: Biological Sciences. Vol. 21, Pg. 342, 1962.
mouse LD50 subcutaneous 880mg/kg (880mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE Sapporo Igaku Zasshi. Sapporo Medical Journal. Vol. 3, Pg. 73, 1952.
rabbit LD50 skin 2650mg/kg (2650mg/kg)   Food and Cosmetics Toxicology. Vol. 13, Pg. 757, 1975.
rat LD50 oral 3450mg/kg (3450mg/kg)   Food and Cosmetics Toxicology. Vol. 13, Pg. 757, 1975.

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