Citronellyl acetate supplier

Name
Citronellyl acetate
EINECS 205-775-0
CAS No. 150-84-5
Article Data41
CAS DataBase
Density 0.885 g/cm³
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
Appearance clear colorless liquid
Safety 24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols
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);
PSA 26.30000
LogP 3.32210

Synthetic route

: 106-22-9
Citronellol

: 108-24-7
acetic anhydride

: 150-84-5
citronellyl-acetate

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With pyridine; toluene-4-sulfonic acid In dichloromethane	98%

: 106-22-9
Citronellol

: 581-55-5
benzylidene 1,1-diacetate

: 150-84-5
citronellyl-acetate

Conditions

Conditions	Yield
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

Conditions	Yield
With thionyl chloride; triethylamine In dichloromethane at 25℃;	90%

: 2466-76-4
N-Acetylimidazole

: 106-22-9
Citronellol

: 150-84-5
citronellyl-acetate

Conditions

Conditions	Yield
Ambient temperature;	63%

: 106-22-9
Citronellol

: 150-84-5
citronellyl-acetate

Conditions

Conditions	Yield
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

Conditions	Yield
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

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

: (6-acetoxy-1-isopropenyl-4-methylhexyl)dimethylsulfonium perchlorate

A: 150-84-5
citronellyl-acetate

B: 141-11-7
3,7-dimethyl-7-octen-1-ol acetate

C: 161013-76-9
3,7-Dimethyl-6-methylthiooct-7-en-1-ol acetate

Conditions

Conditions	Yield
With lithium perchlorate In N,N-dimethyl-formamide E = -1.7 V; Yields of byproduct given;	A n/a B n/a C 15%

...Expand

: (6-acetoxy-1-isopropenyl-4-methylhexyl)dimethylsulfonium perchlorate

A: 150-84-5
citronellyl-acetate

B: 141-11-7
3,7-dimethyl-7-octen-1-ol acetate

C: 3,7,10,14-tetramethylhexadeca-6,10-diene-1,16-diol diacetate

Conditions

Conditions	Yield
With lithium perchlorate In N,N-dimethyl-formamide E = -1.25 V; Yields of byproduct given;	A n/a B n/a C 10%
With lithium perchlorate In N,N-dimethyl-formamide Product distribution; Mechanism; various electrode potentials;

...Expand

: 106-22-9
Citronellol

: 79-20-9
acetic acid methyl ester

: 150-84-5
citronellyl-acetate

Conditions

Conditions	Yield
With Mucor miehei lipase at 40 - 45℃; for 8h;

: 106-22-9
Citronellol

: 123-86-4
acetic acid butyl ester

: 150-84-5
citronellyl-acetate

Conditions

Conditions	Yield
With Mucor miehei lipase at 55 - 60℃; for 18h;

: 106-22-9
Citronellol

: 141-78-6
ethyl acetate

: 150-84-5
citronellyl-acetate

Conditions

Conditions	Yield
With Mucor miehei lipase at 55 - 60℃; for 8h;
With Candida rugosa lipase In toluene at 40℃; for 96h; Time; Enzymatic reaction;	100 %Spectr.
With immobilized enzyme Novozym 435® at 50℃; for 0.133333h; Enzymatic reaction;

: 2280-44-6
D-Glucose

: 106-22-9
Citronellol

: 150-84-5
citronellyl-acetate

Conditions

Conditions	Yield
With culture medium; Hansenula saturnus IFO 0809; sodium acetate In decane; water at 30℃; for 96h; Product distribution; Further Variations:; Reagents; reagent concentration;

: 109164-96-7
1,15-diacetoxy-6-(2'-hydroxy-2'-propyl)-3,9,13-trimethyl-7-selenapentadec-9-ene

: 150-84-5
citronellyl-acetate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / MeI / tetrahydrofuran / 2 h / Heating 2: 90 percent / SOCl2, Et3N / CH2Cl2 / 25 °C View Scheme

: 108-05-4
vinyl acetate

: 106-22-9
Citronellol

: 150-84-5
citronellyl-acetate

Conditions

Conditions	Yield
With steapsin lipase In hexane at 55℃; for 24h; Enzymatic reaction;	94 %Chromat.

: 106-22-9
Citronellol

: 105-46-4
sec-Butyl acetate

: 150-84-5
citronellyl-acetate

Conditions

Conditions	Yield
With zinc(II) oxide at 120℃; for 3h;

: 108-22-5
Isopropenyl acetate

: 106-22-9
Citronellol

: 150-84-5
citronellyl-acetate

Conditions

Conditions	Yield
With methanesulfonic acid; lithium chloride at 80℃; under 760.051 Torr; for 5h;

: 106-22-9
Citronellol

: 3249-50-1
1-propenyl acetate

: 150-84-5
citronellyl-acetate

Conditions

Conditions	Yield
With dimethylphosphoric acid; lithium chloride at 65℃; under 760.051 Torr; for 6h;

: 50-00-0
formaldehyd

: 150-84-5
citronellyl-acetate

: 84143-54-4
Acetic acid 6-hydroxymethyl-3,7-dimethyl-oct-7-enyl ester

Conditions

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at 0℃; for 1h;	98.5%

: 150-84-5
citronellyl-acetate

: 26759-58-0
(+/-)-8-acetoxy-2,3-dihydroxy-2,6-dimethyloctane

Conditions

Conditions	Yield
With N-methyl-2-indolinone; fluorous OsO4 In water; acetone; tert-butyl alcohol at 20℃; for 36h;	97%
With ruthenium trichloride; sodium periodate In water; ethyl acetate; acetonitrile at 0℃; for 0.05h;	67%
With ruthenium trichloride; sodium periodate In ethyl acetate; acetonitrile for 0.05h;	67%
With tert.-butylhydroperoxide; osmium(VIII) oxide; tetraethylammonium chloride; sodium acetate In acetone; tert-butyl alcohol

: 150-84-5
citronellyl-acetate

: 1787-98-0
6,7-epoxycitronellyl acetate

Conditions

Conditions	Yield
With (NMe4)(Co-ortho-phenylenebis(N'-methyloxamidate)2H2OCH3CN; oxygen; pivalaldehyde In fluorobenzene for 1.25h; Ambient temperature;	96%
With sodium acetate; bis[3,5-bis(trifluoromethyl)diphenyl] diselenide In 2,2,2-trifluoroethanol at 20℃; for 0.5h;	95%
With 2*4H2O; oxygen; pivalaldehyde In fluorobenzene for 2.5h;	90%

: 150-84-5
citronellyl-acetate

: 1787-98-0, 73367-94-9, 73367-95-0, 130790-59-9
(3RS,6RS)-6,7-Epoxycitronellyl Acetate

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform 1.) 0 deg C, 2.) 24 h, room temp.;	95%

: 150-84-5
citronellyl-acetate

: 67-68-5
dimethyl sulfoxide

: 407-25-0
trifluoroacetic anhydride

: (6-acetoxy-1-isopropenyl-4-methylhexyl)dimethylsulfonium perchlorate

Conditions

Conditions	Yield
With lithium perchlorate In dichloromethane at 0℃;	95%

...Expand

: 150-84-5
citronellyl-acetate

: 67-68-5
dimethyl sulfoxide

: 407-25-0
trifluoroacetic anhydride

: 123564-19-2
Dimethyl(8-acetoxy-2,6-dimethyloct-1-en-3-yl)sulfonium Trifluoroacetate

Conditions

Conditions	Yield
In dichloromethane at 0℃;	95%

...Expand

: 150-84-5
citronellyl-acetate

A: 5523-95-5, 20780-49-8
3,7-dimethyloctyl acetate

B: 110109-63-2
3,7-dimethyl-7-trifluoroacetoxyoctyl acetate

Conditions

Conditions	Yield
With triethylsilane; lithium perchlorate; trifluoroacetic acid In various solvent(s) at 20℃; for 22h;	A 90% B 1%

: 150-84-5
citronellyl-acetate

: 6-acetoxy-4-methylhexanal

Conditions

Conditions	Yield
With ozone In dichloromethane at -78℃;	90%
With ozone In dichloromethane at -78℃;	90%

: 150-84-5
citronellyl-acetate

: 5-hydroperoxy-3,7-dimethyloct-6-en-1-yl acetate

Conditions

Conditions	Yield
With N-hydroxyphthalimide; iron(III)-acetylacetonate; oxygen In acetonitrile at 20℃; under 760.051 Torr; for 24h;	90%

: 150-84-5
citronellyl-acetate

: 74514-34-4
Acetic acid 6-chloro-3,7-dimethyl-oct-7-enyl ester

Conditions

Conditions	Yield
With sodium chloride In dichloromethane; water for 4h; Ambient temperature; electrolysis by using Pt foils at constant current (50 mA);	86%
With sodium chloride In dichloromethane; water at 25℃; for 0.3h; electrolysis: ruthenium oxide: anode; titanium cylinder: cathode; I = 0.94 A;	84%
With chlorine In tetrachloromethane at 0℃; for 0.583333h;	67%

: 150-84-5
citronellyl-acetate

: 79763-09-0
(E)-3,7-dimethyl-8-oxooct-6-enyl acetate

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; selenium(IV) oxide; silica gel In dichloromethane for 0.166667h; Irradiation;	85%
With tert.-butylhydroperoxide In dichloromethane; water at 20℃; for 24h; Reagent/catalyst; Solvent; Temperature;	60%
With tert.-butylhydroperoxide; selenium(IV) oxide In toluene for 120h; Ambient temperature;

: 150-84-5
citronellyl-acetate

: 96740-50-0
acetoxy-8 dimethyl-2,6 octene-2 al

Conditions

Conditions	Yield
With selenium(IV) oxide; urea-hydrogen peroxide In water; isopropyl alcohol for 0.0111111h; microwave irradiation;	85%

: 67-56-1
methanol

: 150-84-5
citronellyl-acetate

: 868552-81-2
(+/-)-(E)-8-methoxy-2,6-dimethyl-2-methoxy-3-octene

Conditions

Conditions	Yield
With diphenyl diselenide; magnesium sulfate at 66 - 68℃; electrolysis under a constant current 6.7 mA/cm2;	82%

: 150-84-5
citronellyl-acetate

A: 74514-34-4
Acetic acid 6-chloro-3,7-dimethyl-oct-7-enyl ester

B: 122571-72-6
Acetic acid 6,7-dichloro-3,7-dimethyl-octyl ester

Conditions

Conditions	Yield
With pyridine; sulfuryl dichloride In dichloromethane at -60℃;	A 82% B n/a

: 150-84-5
citronellyl-acetate

: 91464-78-7
Acetic acid (E)-7-hydroxy-3,7-dimethyl-oct-5-enyl ester

Conditions

Conditions	Yield
With diphenyl diselenide; water; magnesium sulfate In acetonitrile at 66 - 68℃; electrolysis under a constant current 6.7 mA/cm2;	80%

: 150-84-5
citronellyl-acetate

: 1663-39-4
tert-Butyl acrylate

: 1309476-96-7
t-butyl (E)-8-acetoxy-6-methyloct-2-enoate

Conditions

Conditions	Yield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; toluene-4-sulfonic acid In water at 22℃; for 12h; Sealed vial; Inert atmosphere;	80%

: 150-84-5
citronellyl-acetate

: 103-11-7
2-Ethylhexyl acrylate

: 1309476-97-8
2-ethylhexyl (E)-8-acetoxy-6-methyloct-2-enoate

Conditions

Conditions	Yield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; toluene-4-sulfonic acid In water at 22℃; for 12h; Sealed vial; Inert atmosphere;	78%

: 150-84-5
citronellyl-acetate

: (E)-7-hydroperoxy-3,7-dimethyl-5-octen-1-yl acetate

Conditions

Conditions	Yield
	75.2%

: 150-84-5
citronellyl-acetate

: 69226-51-3
2,2,2-trichloroethyl sulfamate

: acetic acid 5-[3,3-dimethyl-1-(2,2,2-trichloro-ethoxysulfonyl)-aziridin-2-yl]-3-methyl-pentyl ester

Conditions

Conditions	Yield
Stage #1: citronellyl-acetate; 2,2,2-trichloroethyl sulfamate With tetra(trifluoroacetamidato)dirhodium(II); magnesium oxide In benzene at 0℃; Stage #2: With [bis(acetoxy)iodo]benzene In benzene at 0 - 25℃; for 8h; Further stages.;	72%

: 150-84-5
citronellyl-acetate

: 4-methoxybenzyl 4-iodobutanoate

: 4-methoxybenzyl 11-acetoxy-5,5,9-trimethylundecanoate

Conditions

Conditions	Yield
With bis(acetylacetonate)nickel(II); manganese(III) (Z)-2,2,6,6-tetramethyl-5-oxohept-3-en-3-olate; 1,1,1,3',3',3'-hexafluoro-propanol; phenylsilane; potassium carbonate In 1,2-dichloro-ethane at 0 - 20℃; for 24h; Sealed tube;	71%

: 150-84-5
citronellyl-acetate

A: C12H22O4

B: 6-peroxy-7(9)-dehydro-2,3,6,7-tetrahydrogeranyl acetate

Conditions

Conditions	Yield
With bis(dimethyl-di-n-octylammonium) molybdate; dihydrogen peroxide In cyclohexane; water at 25℃; for 6.6h;	A 66% B n/a

: 79-43-6
dichloro-acetic acid

: 150-84-5
citronellyl-acetate

A: 5523-95-5, 20780-49-8
3,7-dimethyloctyl acetate

B: Dichloro-acetic acid 7-acetoxy-1,1,5-trimethyl-heptyl ester

Conditions

Conditions	Yield
With triethylsilane; lithium perchlorate at 20℃; for 48h;	A 65% B 20%

...Expand

: 150-84-5
citronellyl-acetate

: 2-iodoethyl tetrahydro-2H-pyran-4-carboxylate

: 9-acetoxy-3,3,7-trimethylnonyl tetrahydro-2H-pyran-4-carboxylate

Conditions

Conditions	Yield
With bis(acetylacetonate)nickel(II); manganese(III) (Z)-2,2,6,6-tetramethyl-5-oxohept-3-en-3-olate; 1,1,1,3',3',3'-hexafluoro-propanol; phenylsilane; potassium carbonate In 1,2-dichloro-ethane at 0 - 20℃; for 30h; Sealed tube;	65%

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.

Product Name

Citronellyl acetate

Synthetic route

Citronellyl acetate Consensus Reports

Citronellyl acetate Specification

Related Products

Hot Products