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542-46-1

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Basic Information
CAS No.: 542-46-1
Name: CIVETONE
Article Data: 24
Molecular Structure:
Molecular Structure of 542-46-1 (CIVETONE)
Formula: C17H30O
Molecular Weight: 250.425
Synonyms: 9-Cycloheptadecen-1-one,(9Z)-;(Z)-9-Cycloheptadecen-1-one;Civetone;Civettone, alpha-trans-;FEMA No. 3425;9-Cycloheptadecen-1-one, (9Z)-;(9Z)-cycloheptadec-9-en-1-one;9-Cycloheptadecen-1-one, (Z)-;3-07-00-00524 (Beilstein Handbook Reference);9-Cycloheptadecen-1-one, cis-;9-CYCLOHEPTADECEN-1-ONE, (Z)-(8CI,9CI);
EINECS: 208-813-4
Density: 0.859 g/cm3
Melting Point: 31-32°
Boiling Point: 371.4 °C at 760 mmHg
Flash Point: 157.1 °C
Hazard Symbols: Xi
Risk Codes: 38
Safety: 36/37
PSA: 17.07000
LogP: 5.58670
Synthetic route
365439-63-0

(Z)-2-methoxycarbonyl-9-cycloheptadecenoate

542-46-1

(Z)-civetone

Conditions
ConditionsYield
Stage #1: (Z)-2-methoxycarbonyl-9-cycloheptadecenoate With sodium hydroxide In methanol for 1h; Heating;
Stage #2: With sulfuric acid In methanol for 0.5h; pH=1; Heating; Further stages.;
95%
With sulfuric acid In sodium hydroxide; ethanol95%
32357-36-1

cycloheptadec-9-yn-1-one

542-46-1

(Z)-civetone

Conditions
ConditionsYield
With quinoline; hydrogen; Lindlar's catalyst In dichloromethane at 20℃; under 760 Torr; for 2h; Lindlar hydrogenation;94%
With hydrogen; Lindlar's catalyst In hexane for 0.166667h; Ambient temperature;
157622-74-7

2-ethoxycarbonyl-9-cycloheptadecenone

542-46-1

(Z)-civetone

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; ethanol at 80℃; for 5h;93%
91874-18-9

(2E,9Z)-Cycloheptadeca-2,9-dienone

542-46-1

(Z)-civetone

Conditions
ConditionsYield
With sodium bis(2-methoxyethoxy)aluminium dihydride; copper(ll) bromide91%
135618-36-9

nonadeca-1,18-dien-10-one

A

542-46-1

(Z)-civetone

B

1502-37-0

trans-9-Cycloheptadecen-1-one

Conditions
ConditionsYield
With [2-(1-methylethoxy-κO)phenylmethyl-κC](nitrato-κO,κO′){rel-(2R,5R,7S)-tricyclo[3.3.1.13,7]decane-2,1-diyl[3-(2,4,6-trimethylphenyl)-1-imidazolidinyl-2-ylidene]}ruthenium In 1,2-dichloro-ethane at 60℃; under 0.02 Torr; for 8h; Glovebox; Inert atmosphere; stereoselective reaction;A 62%
B n/a
With Grubbs catalyst first generation In dichloromethane for 2h; Inert atmosphere; Reflux; Overall yield = 33 %; Overall yield = 40 mg; diastereoselective reaction;A n/a
B n/a
With hydrogenchloride; C49H54Cl2N4Ru In ethyl acetate at 110℃; for 4h; Inert atmosphere; Schlenk technique; Glovebox; Overall yield = 52 %;A n/a
B n/a
Stage #1: nonadeca-1,18-dien-10-one With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃; for 14h; Reflux; Glovebox; Inert atmosphere;
Stage #2: With ethyl vinyl ether In dichloromethane at 20℃; for 2h; Reagent/catalyst; Solvent; Temperature; Glovebox; Inert atmosphere;
135618-36-9

nonadeca-1,18-dien-10-one

542-46-1

(Z)-civetone

Conditions
ConditionsYield
With C35H47N3O4Ru In dichloromethane at 60℃; for 24h; Sealed tube; Inert atmosphere;36%

1-(aminomethyl)-cyclohexadec-8-enol

A

542-46-1

(Z)-civetone

B

4598-76-9

(Z)-cycloheptadec-8-en-1-one

C

4598-76-9

(E)-cycloheptadec-8-en-1-one

D

1502-37-0

trans-9-Cycloheptadecen-1-one

Conditions
ConditionsYield
With acetic acid; sodium nitrite In water at 5 - 10℃; for 2h; Product distribution / selectivity; Tiffeneau-Demjanov-Reaction; Heating / reflux;A 15%
B 15%
C 32%
D 35%
3100-36-5

(E/Z)-cyclohexa-dec-8-enone

A

542-46-1

(Z)-civetone

B

4598-76-9

(Z)-cycloheptadec-8-en-1-one

C

4598-76-9

(E)-cycloheptadec-8-en-1-one

D

1502-37-0

trans-9-Cycloheptadecen-1-one

Conditions
ConditionsYield
Stage #1: (E/Z)-cyclohexa-dec-8-enone With potassium hydroxide; N-methyl-N-nitrosotoluene-p-sulfonamide In ethanol; water at 3℃; Tiffeneau-Demjanov-Reaction;
Stage #2: With hydrogenchloride In ethanol; water pH=2; Product distribution / selectivity;
A 16%
B 15%
C 33%
D 34%
73125-62-9

(E,E)-2,16-Cycloheptadecadien-9-in-1-on

542-46-1

(Z)-civetone

Conditions
ConditionsYield
With hydrogen; palladium on barium sulfate In pyridine
50768-04-2

9-Cyclononadecinon

542-46-1

(Z)-civetone

Conditions
ConditionsYield
With hydrogen; Lindlar's catalyst In ethyl acetate
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  • Civetone

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    542-46-1

    Civetone

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    542-46-1

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Reported in EPA TSCA Inventory.

Specification

The cis-Civetone is an organic compound with the formula C17H30O. The IUPAC name of this chemical is (9Z)-cycloheptadec-9-en-1-one. With the CAS registry number 542-46-1, it is also named as (Z)-9-cycloheptadecen-1-one. The product's classification code is Skin / Eye Irritant. Besides, it should be stored in a ventilated and cool place.

Physical properties about cis-Civetone are: (1)ACD/LogP: 6.48; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.48; (4)ACD/LogD (pH 7.4): 6.48; (5)ACD/BCF (pH 5.5): 49384.45; (6)ACD/BCF (pH 7.4): 49384.45; (7)ACD/KOC (pH 5.5): 79662.46; (8)ACD/KOC (pH 7.4): 79662.46; (9)#H bond acceptors: 1; (10)Polar Surface Area: 17.07 Å2; (11)Index of Refraction: 1.448; (12)Molar Refractivity: 78.13 cm3; (13)Molar Volume: 291.3 cm3; (14)Polarizability: 30.97×10-24cm3; (15)Surface Tension: 28.6 dyne/cm; (16)Density: 0.859 g/cm3; (17)Flash Point: 157.1 °C; (18)Enthalpy of Vaporization: 61.84 kJ/mol; (19)Boiling Point: 371.4 °C at 760 mmHg; (20)Vapour Pressure: 1.04E-05 mmHg at 25°C.

Preparation: the civet liquid caustic soda by 10% KOH-based ethanol, will be the neutral part of the vacuum distillation, collecting 130-170 °C (0.2kPa) fractions, converting them into ammonia urea reduction, separation refining, and then oxalic acid decomposition, may civet ketone. Ketones in the separation of civet civet residue also contains mellow, phthalates can be used to isolate and alkalization, and then use chromic acid oxidation of ketones derived from civet. Synthesis method can be extracted from natural shellac obtained 9,10,16 - trihydroxy-16 acid as raw material, halogenated, elimination of chloride of thionyl chloride, and ethyl acetoacetate condensation, decarboxylation, esterification, iodine cyclization, hydrolysis and other steps to be obtained; It also available from the starting system of oleic acid or 11 to take the goods.

Uses of cis-Civetone: it is used to sulan heart, oriental flavor, citrus Cologne and many floral type, such as large flower jasmine, prynne, narcissus, rose essence and is useful for fixed deodorant. It is indispensable for the preparation of artificial civet spices, the general amount of 1% -2%. It is also used as a substitute for musk. It has a strong ability to be fragrant and often act to deodorant. It can be used for blending high-level essence, in the perfume in the amount of 0.04-0.4% in the balm and lotion in the amount of 0.003-0.02%.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1CCCCCCC\C=C/CCCCCCC1
(2)InChI: InChI=1/C17H30O/c18-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-17/h1-2H,3-16H2/b2-1-
(3)InChIKey: ZKVZSBSZTMPBQR-UPHRSURJBS
(4)Std. InChI: InChI=1S/C17H30O/c18-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-17/h1-2H,3-16H2/b2-1-
(5)Std. InChIKey: ZKVZSBSZTMPBQR-UPHRSURJSA-N