Cyclopentadecanolide supplier

Name
Cyclopentadecanolide
EINECS 203-354-6
CAS No. 106-02-5
Article Data122
CAS DataBase
Density 0.885 g/cm³
Solubility Soluble in six volume 80% or 90% ethanol
Melting Point 34-38 °C(lit.)
Formula C₁₅H₂₈O₂
Boiling Point 344.797 °C at 760 mmHg
Molecular Weight 240.386
Flash Point 143.392 °C
Transport Information
Appearance white crystalline low melting solid
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Pentadecanoicacid, 15-hydroxy-, x-lactone (6CI,7CI);1,15-Pentadecanolide;1-Oxacyclohexadecan-2-one;15-Hydroxypentadecanoic acid lactone;15-Pentadecanolide;15-Pentadodecanolactone;2-Pentadecalone;CPE 215;Oxacyclohexadecan-2-one;Exaltolide;Muskalactone;NSC 36763;Pentadecalactone;Pentadecanolactone;Pentadecanolide;Pentalide;Thibetolide;cpd Supra;w-Pentadecalactone;
PSA 26.30000
LogP 4.61450

Synthetic route

: 15-pentadecyn-2-olide

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
With hydrogen; platinum(IV) oxide	100%

: 4617-33-8
15-hydroxylpentadecanoic acid

A: 106-02-5
pentadecanolide

B: 659-76-7
1,17-dioxa-cyclodotriacontane-2,18-dione

Conditions

Conditions	Yield
With p-nitrobenzoic anhydride; scandium tris(trifluoromethanesulfonate) In tetrahydrofuran; acetonitrile Heating; Yields of byproduct given;	A 99% B n/a
With dmap; 2-methyl-6-nitrobenzoic anhydride In dichloromethane at 20℃; for 15h;	A 92% B 1%
With dmap; di-2-thienyl carbonate; hafnium(IV) trifluoromethanesulfonate In toluene; acetonitrile at 100℃; for 5h;	A 92% B n/a

: 63294-84-8
(E)-6-pentadecen-15-olide

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
With hydrogen; palladium-barium carbonate under 1520 Torr; for 3h; Ambient temperature;	99%

: 76293-72-6, 76293-73-7, 4941-77-9
(E/Z)-oxacyclohexadec-11-en-2-one

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
With palladium on activated charcoal; hydrogen In ethyl acetate at 20℃; under 760.051 Torr; for 16h; Solvent; Concentration; Schlenk technique; Glovebox;	99%
With hydrogen; palladium on activated charcoal under 760 Torr;	94%
With hydrogen; palladium on activated charcoal	94%
With hydrogen; platinum(IV) oxide under 760 Torr;
With 5%-palladium/activated carbon; hydrogen In methanol at 25℃; for 24h;	89.2 %Chromat.

: 87227-39-2
E-Pentadec-2-ene-15-olide

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal	99%
With hydrogen; palladium on activated charcoal In ethyl acetate at 20℃; under 760 Torr; for 3h;	98%
With hydrogen; palladium on activated charcoal In ethanol; ethyl acetate for 48h; Ambient temperature;	48 mg

: 4617-33-8
15-hydroxylpentadecanoic acid

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
With dmap; polymer bound carbodiimide; 4-(dimethylamino)pyridine hydrochloride In tetrahydrofuran; chloroform Cyclization; lactonisation; Heating;	97%
With dmap; 4-(dimethylamino)pyridine hydrochloride; dicyclohexyl-carbodiimide In tetrahydrofuran; chloroform Heating;	95%
With dmap; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In tetrahydrofuran; chloroform for 18h; Reflux; Inert atmosphere;	95%

: 195320-68-4
(Z)-Oxacyclohexadec-6-en-2-one

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal under 760 Torr;	95%
With hydrogen; palladium on activated charcoal	95%

: 93472-40-3
trimethylsilyl 15-(trimethylsiloxy)pentadecanoate

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
dipropylboryl triflate In toluene Heating;	94%

: 15-hydroxypentadecanoic acid butyl ester

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
With titanium(IV) isopropylate at 70 - 250℃; under 3.75038 Torr; for 0.333333h; Reagent/catalyst; Inert atmosphere;	92.9%

: 118072-05-2
12-iodo-15-pentadecanolide

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Irradiation;	92%
With 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene 1.) THF, reflux, 40 min, 2.) THF, ether; Multistep reaction;

: (14-Carboxy-tetradecyl)-diphenyl-sulfonium; perchlorate

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
With potassium carbonate In acetone for 12h; Heating;	92%
With potassium carbonate In acetone for 48h; Heating; Yield given;

: 1-(N,4-dimethylphenylsulfonylamino)vinyl 15-hydroxypentadecanoate

A: 106-02-5
pentadecanolide

B: 16697-83-9
N-methyl-N-tosylacetamide

Conditions

Conditions	Yield
With camphor-10-sulfonic acid In dichloromethane at 20℃; for 4h;	A 92% B n/a

: 1-(N,4-dimethylphenylsulfonylamino)vinyl 15-hydroxypentadecanoate

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 20℃;	92%

: 77744-43-5
15-(tert-butyldimethylsilyloxy)-pentadecanoic acid

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
With tetrabutylammonium tetrafluoroborate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In chloroform for 18h; Reflux; Inert atmosphere;	91%
Multi-step reaction with 4 steps 1.1: n-BuLi / diethyl ether / 0 °C 1.2: (COCl)2; DMF / diethyl ether 2.1: Et3N / CH2Cl2 / 0 - 20 °C 3.1: 96 percent / 3HF*Et3N / acetonitrile / 20 °C 4.1: 58 percent / Cu(OTf)2 / tetrahydrofuran / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: n-BuLi / diethyl ether / 0 °C 1.2: (COCl)2; DMF / diethyl ether 2.1: Et3N / CH2Cl2 / 0 - 20 °C 3.1: 57 percent / 3HF*Et3N / acetonitrile / 20 °C 4.1: 83 percent / Cu(OTf)2 / tetrahydrofuran / 20 °C View Scheme

: 38223-29-9
12-oxo-15-pentadecanolide

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
With hydrogenchloride; zinc In acetic anhydride at 0 - 5℃; for 1h;	90%
With hydrogenchloride; zinc In toluene at 0℃;	84%
With sodium cyanoborohydride; toluene-4-sulfonic acid; toluene-4-sulfonic acid hydrazide 1.) DMF, sulfolane, 15 min., 2.) cyclohexane, reflux, 4 h;	50%
Multi-step reaction with 2 steps 1: methanol / 0.67 h / Heating 2: <<(C6H5)3P>Cu>BH4 / CHCl3 / 4 h / Heating View Scheme

: 89611-22-3
15-Hydroxy-pentadecanoic acid (Z)-2-dimethylcarbamoyl-1-methyl-vinyl ester

A: 106-02-5
pentadecanolide

B: 2044-64-6
N,N-Dimethylacetoacetamid

Conditions

Conditions	Yield
With magnesium bromide In tetrahydrofuran at 55℃; other solvents, temperatures and reagent;	A 90% B n/a

: 81238-39-3
13-Benzenesulfonyl-oxacyclohexadecan-2-one

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
With disodium hydrogenphosphate; sodium amalgam In methanol; 1,2-dimethoxyethane at -25℃; for 3h;	90%

: 109182-98-1
Acrylic acid 12-iodo-dodecyl ester

A: 106-02-5
pentadecanolide

B: 659-76-7
1,17-dioxa-cyclodotriacontane-2,18-dione

Conditions

Conditions	Yield
With sodium cyanoborohydride In methanol for 3h; Ambient temperature; Irradiation;	A 90% B 7 % Chromat.

: 93472-40-3
trimethylsilyl 15-(trimethylsiloxy)pentadecanoate

A: 106-02-5
pentadecanolide

B: 659-76-7
1,17-dioxa-cyclodotriacontane-2,18-dione

Conditions

Conditions	Yield
With 4-(trifluoromethyl)benzoic anhydride; silver perchlorate; titanium tetrachloride In dichloromethane for 3h; Ambient temperature;	A 89% B 4%
With 4-(trifluoromethyl)benzoic anhydride; silver perchlorate; titanium tetrachloride In dichloromethane; toluene at 20℃; for 33h;	A 89% B 2%

: 173790-14-2
Z-oxacyclohexadec-3-en-2-one

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
With samarium diiodide; 2,4-dichlorophenoxyacetic acid dimethylamine; tert-butyl alcohol In tetrahydrofuran for 0.5h; Ambient temperature;	88%

: 76529-42-5
methyl 15-hydroxypentadecanoate

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
With Lipase B immobilized on acrylic resin from Candida antarctica In cyclohexane; water at 40℃; for 2h; Enzymatic reaction;	88%
Multi-step reaction with 4 steps 1: Imidazole / dimethylformamide 2: 5.0 M NaOH / tetrahydrofuran; methanol; H2O / 7 h 3: 1.) DCC, DMAP; 2.) CH3COOH / 1.) THF, -25 deg C, 4 days; 2.) H2O, room temp., 8 h 4: 45 percent Chromat. / t-BuOK / benzene; tetrahydrofuran View Scheme
Multi-step reaction with 4 steps 1: Imidazole / dimethylformamide 2: 5.0 M NaOH / tetrahydrofuran; methanol; H2O / 7 h 3: 1.) DCC, DMAP; 2.) CH3COOH / 1.) THF, -25 deg C, 4 days; 2.) H2O, room temp., 8 h 4: 74 percent / t-BuOK, molecular sieves / benzene; tetrahydrofuran / Heating; also without molecuar sieves and reflux View Scheme
Multi-step reaction with 4 steps 1: Imidazole / dimethylformamide 2: 5.0 M NaOH / tetrahydrofuran; methanol; H2O / 7 h 3: 1.) 1-<3-(Dimethylamino)propyl>-3-ethylcarboximide hydrochloride, DMAP; 2.) CH3COOH / 1.) DMF, 1 day; 2.) H2O, 12 h 4: 81 percent / t-BuOK, molecular sieves / benzene; tetrahydrofuran / Heating; also without molecuar sieves and reflux View Scheme
Multi-step reaction with 4 steps 1: Imidazole / dimethylformamide 2: 5.0 M NaOH / tetrahydrofuran; methanol; H2O / 7 h 3: 1.) DCC, DMAP; 2.) CH3COOH / 1.) THF, -25 deg C, 5 days; 2.) THF-H2O, room temp., 20 h 4: 43 percent Chromat. / t-BuOK, 19-crown-6 / benzene; tetrahydrofuran View Scheme

: 502-72-7
cyclopentadecanone

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 108h;	86%
Stage #1: cyclopentadecanone With N-hydroxyphthalimide; 1,1-Diphenylmethanol; 2,2'-azobis(isobutyronitrile); oxygen In acetonitrile at 75℃; under 760.051 Torr; for 22h; Baeyer-Villiger oxidation; Stage #2: With 1,1,1,3',3',3'-hexafluoro-propanol; toluene-4-sulfonic acid at 60℃; Baeyer-Villiger oxidation; Inert atmosphere;	70%
With potassium peroxomonosulphate; sulfuric acid; Petroleum ether at 50 - 65℃;

: 56523-59-2
15-bromo-pentadecanoic acid

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
With tetraoctylammonium (2-pyrrolidonide) In N,N-dimethyl-formamide for 24h; Ambient temperature;	84%
With potassium carbonate In dimethyl sulfoxide at 75℃; for 4h;	78%
With potassium carbonate; butanone

: 4617-33-8
15-hydroxylpentadecanoic acid

: 14338-32-0
2-chloro-1-methyl-pyridinium iodide

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
With triethylamine In acetonitrile	84%
With tributyl-amine In acetonitrile	74%
With triethylamine In toluene	63%.

: 874583-99-0
15-hydroxy-pentadecanoic acid 6-methyl-pyridin-2-yl ester

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate) In tetrahydrofuran at 20℃;	83%

: 77744-39-9
15-Hydroxy-pentadecanethioic acid S-[(2R,3aR,19aS)-1-(tetradecahydro-4,7,10,13,16,19-hexaoxa-cyclopentacyclooctadecen-2-yl)methyl] ester

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
With molecular sieve; potassium tert-butylate In tetrahydrofuran; benzene Heating;	81%
With molecular sieve; potassium tert-butylate In tetrahydrofuran; benzene Product distribution; Heating; also without molecuar sieves and reflux;	81%

: 122695-16-3
N-nitro-15-pentadecanelactam

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
In tetrachloromethane for 12h; Heating;	80%

: 76529-42-5
methyl 15-hydroxypentadecanoate

A: 106-02-5
pentadecanolide

B: 659-76-7
1,17-dioxa-cyclodotriacontane-2,18-dione

Conditions

Conditions	Yield
In benzene at 40℃; for 72h; Lipase P;	A 78% B n/a
With Lipase P In benzene at 40℃; for 72h; Product distribution;

: 4617-33-8
15-hydroxylpentadecanoic acid

: 2-chloro-1-ethyl-3-methylpyridinium tetrafluoroborate

: 106-02-5
pentadecanolide

Conditions

Conditions	Yield
With triethylamine In acetonitrile	78%

: 67-56-1
methanol

: 106-02-5
pentadecanolide

: 76529-42-5
methyl 15-hydroxypentadecanoate

Conditions

Conditions	Yield
With sulfuric acid Reflux;	100%
With sulfuric acid Reflux;	100%
With toluene-4-sulfonic acid for 24h; Esterification; Ring cleavage; Heating;	99%

: 106-02-5
pentadecanolide

: 4617-33-8
15-hydroxylpentadecanoic acid

Conditions

Conditions	Yield
With (Z)-9-octadecen-1-amine; lipase PS from Pseudomonas cepacia; water In Hexadecane at 40℃; for 0.5h; Miniemulsion system; Enzymatic reaction;	100%
With sodium hydroxide In tetrahydrofuran; methanol; water	100%
With potassium hydroxide In methanol; water for 5.5h; Heating;	99%

: 106-02-5
pentadecanolide

: 71736-22-6
15-iodo-pentadecanoic acid

Conditions

Conditions	Yield
With hydrogen iodide In acetic acid for 3h; Ring cleavage; iodination; Heating;	100%
With aluminium(III) iodide In acetonitrile at 80℃; for 18h;	99%
With hydrogen iodide In acetic acid for 6h; Heating;	93%

: 106-02-5
pentadecanolide

: 871570-58-0
potassium 15-hydroxypentadecanoate

Conditions

Conditions	Yield
With ethanol; potassium hydroxide for 2h; Reflux;	100%
With potassium hydroxide In ethanol for 2h; Reflux;	100%
With potassium hydroxide In ethanol for 2h; Reflux;	100%
With potassium hydroxide In methanol

: 106-02-5
pentadecanolide

: 124-41-4
sodium methylate

: 76529-42-5
methyl 15-hydroxypentadecanoate

Conditions

Conditions	Yield
In methanol at 20℃; for 16h; Inert atmosphere; Darkness;	99%
In methanol at 20℃;	80%

: 106-02-5
pentadecanolide

: 14722-40-8
1,15-pentadecanediol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 72h;	98.6%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere;	97%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere;	96%

: 106-02-5
pentadecanolide

: 56523-59-2
15-bromo-pentadecanoic acid

Conditions

Conditions	Yield
With sulfuric acid; hydrogen bromide for 84h; Heating;	98%
With hydrogen bromide; acetic acid at 60℃; for 16h; Product distribution / selectivity; Autoclave; Inert atmosphere;	91%
With sulfuric acid; hydrogen bromide for 20h; Heating;	84%

: 67-56-1
methanol

: 106-02-5
pentadecanolide

: 124-41-4
sodium methylate

: 76529-42-5
methyl 15-hydroxypentadecanoate

Conditions

Conditions	Yield
for 3h; Heating / reflux;	98%

...Expand

: 106-02-5
pentadecanolide

: 75-16-1
methylmagnesium bromide

: 728935-75-9
15-methylhexadecan-1,15-diol

Conditions

Conditions	Yield
Stage #1: pentadecanolide; methylmagnesium bromide In tetrahydrofuran at -78 - 20℃; for 16h; Inert atmosphere; Stage #2: With acetic acid In tetrahydrofuran; water Cooling with ice;	98%

: 120-72-9
indole

: 106-02-5
pentadecanolide

: 74022-43-8
ω-(3-indolyl)pentadecanoic acid

Conditions

Conditions	Yield
With sodium hydroxide at 250℃; for 18h; Product distribution; autoclave, other base, other temperature;	95%

: 106-02-5
pentadecanolide

: 2524-64-3
chlorophosphoric acid diphenyl ester

: Phosphoric acid (E)-(oxacyclohexadec-2-en-2-yl) ester diphenyl ester

Conditions

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hexamethylsilazane In tetrahydrofuran at -78℃; for 0.5h;	91%

: 106-02-5
pentadecanolide

: 111-86-4
n-Octylamine

: 1220909-19-2
N-octyl-15-hydroxypentadecanoylamine

Conditions

Conditions	Yield
With lipase PS from Pseudomonas cepacia; water In Hexadecane at 40℃; for 192h; Miniemulsion system; Enzymatic reaction;	91%

Cyclopentadecanolide Specification

The Cyclopentadecanolide, with the CAS registry number 106-02-5, is also known as 15-Hydroxypentadecanoic acid lactone. Its EINECS number is 203-354-6. This chemical's molecular formula is C₁₅H₂₈O₂ and molecular weight is 240.38. What's more, its systematic name is Oxacyclohexadecan-2-one. This chemical should be sealed and stored in a cool and ventilated place. Moreover, it should be protected from oxides, light, heat and fire. It plays a role of fixing agent in the essence. It is suitable for eastern and fantasy type essences, such as potpourri, elecampane and ambre. When using it, you must avoid contact with eyes.

Physical properties of Cyclopentadecanolide are: (1)ACD/LogP: 5.166; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.17; (4)ACD/LogD (pH 7.4): 5.17; (5)ACD/BCF (pH 5.5): 4969.45; (6)ACD/BCF (pH 7.4): 4969.45; (7)ACD/KOC (pH 5.5): 15396.09; (8)ACD/KOC (pH 7.4): 15396.09; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 26.3 Å²; (13)Index of Refraction: 1.436; (14)Molar Refractivity: 70.912 cm³; (15)Molar Volume: 271.377 cm³; (16)Polarizability: 28.112×10^-24cm³; (17)Surface Tension: 28.47 dyne/cm; (18)Density: 0.886 g/cm³; (19)Flash Point: 143.392 °C; (20)Enthalpy of Vaporization: 58.88 kJ/mol; (21)Boiling Point: 344.797 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by 15-hydroxy-pentadecanoic acid at the ambient temperature. This reaction will need reagents N,N,N'-N'-tetramethylurea, oxalyl chloride, collidine and solvents acetonitrile, diethyl ether with the reaction time of 46 hours. The yield is about 90%.

Cyclopentadecanolide can be prepared by 15-hydroxy-pentadecanoic acid at the ambient temperature

Uses of Cyclopentadecanolide: it can be used to produce 15-iodo-pentadecanoic acid by heating. It will need reagent HI and solvent acetic acid with the reaction time of 3 hours. The yield is about 100%.

Cyclopentadecanolide can be used to produce 15-iodo-pentadecanoic acid by heating

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1OCCCCCCCCCCCCCC1
(2)Std. InChI: InChI=1S/C15H28O2/c16-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-17-15/h1-14H2
(3)Std. InChIKey: FKUPPRZPSYCDRS-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rabbit	LD50	skin	> 5gm/kg (5000mg/kg)		Food and Cosmetics Toxicology. Vol. 13, Pg. 787, 1975.
rat	LD50	oral	> 5gm/kg (5000mg/kg)		Food and Cosmetics Toxicology. Vol. 13, Pg. 787, 1975.

Product Name

Cyclopentadecanolide

Synthetic route

Cyclopentadecanolide Specification

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