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Citronellyl acetate

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Name

Citronellyl acetate

EINECS 205-775-0
CAS No. 150-84-5 Density 0.885 g/cm3
PSA 26.30000 LogP 3.32210
Solubility practically insoluble in water Melting Point 17.88°C (estimate)
Formula C12H22O2 Boiling Point 258.5 °C at 760 mmHg
Molecular Weight 198.305 Flash Point 88.2 °C
Transport Information N/A Appearance clear colorless liquid
Safety 24/25 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 150-84-5 (Citronellyl acetate) Hazard Symbols N/A
Synonyms

Citronellol acetate (6CI);1-Acetoxy-3,7-dimethyloct-6-ene;3,7-Dimethyl-6-octen-1-yl acetate;8-Acetoxy-2,6-dimethyl-2-octene;Cephrol acetate;NSC4893;dl-Citronellol acetate;b-Citronellol acetate;b-Citronellyl acetate;67650-82-2;6-Octen-1-ol,3,7-dimethyl-, acetate (7CI,8CI,9CI);

Article Data 41

Citronellyl acetate Synthetic route

106-22-9

Citronellol

108-24-7

acetic anhydride

150-84-5

citronellyl-acetate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃;100%
With C12H8N2*2CH4O3S at 60℃; for 3h;99%
With iodine at 25℃; for 0.0166667h;98%
106-22-9

Citronellol

64-19-7

acetic acid

150-84-5

citronellyl-acetate

Conditions
ConditionsYield
With Candida antarctica lipase B at 50℃; for 4h; Molecular sieve; Ionic liquid; Green chemistry; Enzymatic reaction;99.9%
With cetyltrimethylammonium chloride; potassium hexacyanoferrate(III) at 80℃; for 1h;90%
With molecular sieve at 120℃; for 8h;
106-22-9

Citronellol

75-36-5

acetyl chloride

150-84-5

citronellyl-acetate

Conditions
ConditionsYield
With potassium fluoride on basic alumina In toluene for 1h;98%
7540-51-4

(S)-3,7-dimethyl-6-octen-1-ol

108-24-7

acetic anhydride

150-84-5

citronellyl-acetate

Conditions
ConditionsYield
With pyridine; toluene-4-sulfonic acid In dichloromethane98%
106-22-9

Citronellol

581-55-5

benzylidene 1,1-diacetate

150-84-5

citronellyl-acetate

Conditions
ConditionsYield
With potassium carbonate at 90℃; for 16h;92%
109143-32-0

8-acetoxy-2,6-dimethyl-3-methylseleno-2-hydroxyoctane

150-84-5

citronellyl-acetate

Conditions
ConditionsYield
With thionyl chloride; triethylamine In dichloromethane at 25℃;90%
2466-76-4

N-Acetylimidazole

106-22-9

Citronellol

150-84-5

citronellyl-acetate

Conditions
ConditionsYield
Ambient temperature;63%
106-22-9

Citronellol

150-84-5

citronellyl-acetate

Conditions
ConditionsYield
With tin(ll) chloride In water; acetic acid for 17h; Ambient temperature;57%
With Pichia kluyveri NBRC 1165; S-acetyl coenzyme A In decane for 288h;
106-22-9

Citronellol

75-05-8

acetonitrile

150-84-5

citronellyl-acetate

Conditions
ConditionsYield
With Bromotrichloromethane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate at 20℃; for 12h; Irradiation; Inert atmosphere;52%
64-17-5

ethanol

106-23-0, 26489-02-1

3,7-dimethyl-oct-6-enal

150-84-5

citronellyl-acetate

Conditions
ConditionsYield
With potassium tert-butylate In 1,4-dioxane at 120℃; for 65h;45%

Citronellyl acetate Consensus Reports

Reported in EPA TSCA Inventory.

Citronellyl acetate Specification

The Acetic acid, citronellyl ester, with its CAS registry number 150-84-5, has the IUPAC name of 3,7-dimethyloct-6-enyl acetate. For being a kind of clear colourless liquid, it is practically insoluble in water, and its product categories are including Acyclic Monoterpenes; Biochemistry; Terpenes; Alphabetical Listings; C-D; Flavors and Fragrances. When comes to its production method, it could be made from the esterification of the citronellol, acetic anhydride, and anhydrous sodium acetate with its yield of 85%. What's more, while using, you should avoid contacting with skin and eyes.

The characteristics of Acetic acid, citronellyl ester are as follows: (1)ACD/LogP: 4.28; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.28; (4)ACD/LogD (pH 7.4): 4.28; (5)ACD/BCF (pH 5.5): 1049.84; (6)ACD/BCF (pH 7.4): 1049.84; (7)ACD/KOC (pH 5.5): 5059.63; (8)ACD/KOC (pH 7.4): 5059.63; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 26.3; (13)Index of Refraction: 1.442; (14)Molar Refractivity: 59.27 cm3; (15)Molar Volume: 223.8 cm3; (16)Polarizability: 23.49×10-24 cm3; (17)Surface Tension: 28 dyne/cm; (18)Density: 0.885 g/cm3; (19)Flash Point: 88.2 °C; (20)Enthalpy of Vaporization: 49.61 kJ/mol; (21)Boiling Point: 258.5 °C at 760 mmHg; (22)Vapour Pressure: 0.0137 mmHg at 25°C; (23)Exact Mass: 198.16198; (24)MonoIsotopic Mass: 198.16198; (25)Topological Polar Surface Area: 26.3; (26)Heavy Atom Count: 14; (27)Complexity: 191.

Use of this chemical: Acetic acid, citronellyl ester could react to produce (+/-)-8-acetoxy-2,3-dihydroxy-2,6-dimethyloctane. This reaction could happen in the presence of the reagent of OsO4, Cl, NaOAc, tBuO2H and the solvent of acetone and 2-methyl-propan-2-ol.

Production method of this chemical: 3,7-dimethyl-oct-6-en-1-ol could react to produce 8-acetoxy-2,6-dimethyl-oct-2-ene. This reaction could happen in the presence of the reagent of SnCl2*2H2O and the solvent of acetic acid and H2O, and this reaction needs 17 hours in the ambient temperature.

As for its usage, it is widely applied in many ways. This chemical is mainly used in the application of modulation roses, lavender, apple, banana, apricot and citrus flavor. And it is also commonly used in various essential oils, which can increase the sweetness.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: CC(CCC=C(C)C)CCOC(=O)C
(2)InChI: InChI=1S/C12H22O2/c1-10(2)6-5-7-11(3)8-9-14-12(4)13/h6,11H,5,7-9H2,1-4H3
(3)InChIKey: JOZKFWLRHCDGJA-UHFFFAOYSA-N 

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral 6800mg/kg (6800mg/kg)   Food and Cosmetics Toxicology. Vol. 11, Pg. 1069, 1973.

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