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Geraniol

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Name

Geraniol

EINECS 203-377-1
CAS No. 106-24-1 Density 0.867 g/cm3
PSA 20.23000 LogP 2.67140
Solubility practically insoluble in water Melting Point -15 °C
Formula C10H18O Boiling Point 229.499 °C at 760 mmHg
Molecular Weight 154.252 Flash Point 76.667 °C
Transport Information N/A Appearance colourless to pale yellow liquid with an odour of roses
Safety 26-36-24/25 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 106-24-1 (Geraniol) Hazard Symbols IrritantXi
Synonyms

3,7-Dimethyl-trans-2, 6-octadien-1-ol;2,6-Dimethyl-trans-2, 6-octadien-8-ol;trans-Geraniol;Geraniol alcohol;Guaniol;(E)-3,7-dimethylocta-2,6-dien-1-ol;Lemonol;2,6-Octadien-1-ol,3,7-dimethyl-,(2E)-;Geranyl alcohol;Geraniol extra;trans-3,7-Dimethyl-2,6-octadien-1-ol;Nerol;Geraniol;2,6-Dimethyl-2,6-octadien-8-ol;

Article Data 300

Geraniol Synthetic route

141-27-5

3,7-dimethyl-2,6-octadienal

106-24-1

Geraniol

Conditions
ConditionsYield
With phosphotungstic acid; sodium tetrahydroborate In methanol100%
With sodium tetrahydroborate; sodium hydroxide In water at 35℃; for 0.416667h; pH=12; Reagent/catalyst; Green chemistry;99%
antimony(III) chloride; aluminium In water; N,N-dimethyl-formamide for 1h; Ambient temperature;98%
16409-44-2

3,7-dimethylocta-2,6-dien-1-yl ethanoate

106-24-1

Geraniol

Conditions
ConditionsYield
With potassium carbonate In methanol Inert atmosphere;100%
105-87-3

3,7-dimethyl-2E,6-octadien-1-yl acetate

106-24-1

Geraniol

Conditions
ConditionsYield
With potassium carbonate In methanol at 25℃; for 0.166667h;99%
With methanol at 80℃; for 6h; Inert atmosphere; Schlenk technique;99%
With methanol; oxo[hexa(trifluoroacetato)]tetrazinc for 12h; Reflux; Inert atmosphere;96%
92464-82-9

(2E)-3,7-dimethyl-1-triphenylmethoxy-2,6-octadiene

106-24-1

Geraniol

Conditions
ConditionsYield
With naphthalene; lithium In tetrahydrofuran at -78℃; for 1.5h;99%
59632-99-4

geranyl 2-tetrahydropyranyl ether

106-24-1

Geraniol

Conditions
ConditionsYield
With dimethylbromosulphonium bromide In methanol; dichloromethane at 20℃; for 2h;98%
Nafion-H In methanol for 6h;97%
With lithium perchlorate at 55℃; Product distribution; acid catalyst generated by electrolysis;96%
80873-81-0

geraniol tert-butyldimethylsilyl ether

106-24-1

Geraniol

Conditions
ConditionsYield
With Decaborane In tetrahydrofuran; methanol at 20℃; for 1h;98%
With iron(III) chloride In methanol at 20℃; for 0.5h;96%
With iron(III) p-toluenesulfonate hexahydrate In methanol at 20℃; for 2.25h; chemoselective reaction;86%
160882-63-3

{[(2E)-3.7-dimethyl-2,6-octadien-1-yl]oxy}(triethyl)silane

106-24-1

Geraniol

Conditions
ConditionsYield
10percent Pd/C In methanol at 20℃; for 2h;98%
1204225-79-5

C25H32O3

106-24-1

Geraniol

Conditions
ConditionsYield
With ethanol; copper(ll) bromide at 20℃; for 0.5h;98%
72106-90-2

O-(trans-3,7-dimethylocta-2,6-dien-1-yl)trimethylsilane

106-24-1

Geraniol

Conditions
ConditionsYield
Tetrabutyl-1,3-diisothiocyanato-distannoxane In methanol for 16h; Ambient temperature;95%
1,3-di(NCS)-tetrabutyldistannoxane In methanol for 16h; Ambient temperature; Deprotection of silyl ethers;95%
With water; aluminium In hexane for 0.0833333h; Ambient temperature;90%

(E)-3,7-dimethyl-1-(2-phenylallyloxy)-2,6-octadiene

106-24-1

Geraniol

Conditions
ConditionsYield
With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.5h;95%

Geraniol Consensus Reports

Reported in EPA TSCA Inventory.

Geraniol Specification

Geraniol, with the CAS registry number 106-24-1, is also named as 3,7-Dimethyl-trans-2,6-octadien-1-ol. The product's categories are Acyclic Monoterpenes; Biochemistry; Terpenes, and the other registry number is 8007-13-4. Besides, it is colourless to pale yellow liquid with an odour of roses, which should be sealed in brown glass bottles in cool and dark place at 2-8 °C. It can react with oxoacids and carboxylic acids to form esters plus water. In addition, it is stable and incompatible with strong oxidizing agents.

Physical properties about Geraniol are: (1)ACD/LogP: 3.279; (2)ACD/LogD (pH 5.5): 3.28; (3)ACD/LogD (pH 7.4): 3.28; (4)ACD/BCF (pH 5.5): 182.88; (5)ACD/BCF (pH 7.4): 182.88; (6)ACD/KOC (pH 5.5): 1448.34; (7)ACD/KOC (pH 7.4): 1448.34; (8)#H bond acceptors: 1; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 5; (11)Index of Refraction: 1.471; (12)Molar Refractivity: 49.714 cm3; (13)Molar Volume: 177.941 cm3; (14)Polarizability: 19.708 10-24cm3; (15)Surface Tension: 29.1669998168945 dyne/cm; (16)Density: 0.867 g/cm3; (17)Flash Point: 76.667 °C; (18)Enthalpy of Vaporization: 54.187 kJ/mol; (19)Boiling Point: 229.499 °C at 760 mmHg; (20)Vapour Pressure: 0.0130000002682209 mmHg at 25°C;

Preparation of Geraniol: It can be obtained by separation of the plant essential oil. Additionally, this chemical can be prepared by 3,7-Dimethyl-octa-2,6-dienal.



This reaction needs BER and Methanol at temperature of 25 °C. The reaction time is 3 hours. The yield is 90 %.

Uses of Geraniol: This chemical is commonly used in perfumes. It is also used in flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. And it is used as one of the 599 additives to cigarettes to improve their flavor. Besides, it is an effective plant-based mosquito repellent. Furthermore, it can be used to produce Neryl benzyl ether.



This reaction needs NaH and Tetrahydrofuran at ambient temperature for 6 hours. The yield is 70 %.

When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing. Moreover, you should avoid contact with skin and eyes.

People can use the following data to convert to the molecule structure.
(1)InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+;
(2)InChIKey=GLZPCOQZEFWAFX-JXMROGBWSA-N;
(3)SmilesC(\CC\C=C(\C)C)(=C\CO)C;

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 1090mg/kg (1090mg/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 > 5gm/kg (5000mg/kg)   Food and Cosmetics Toxicology. Vol. 12, Pg. 881, 1974.
rabbit LDLo intravenous 50mg/kg (50mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 58, Pg. 394, 1962.
rat LD50 oral 3600mg/kg (3600mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: COMA
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

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