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Cas Database |
| Name |
Cyclopentadecanolide |
EINECS | 203-354-6 |
| CAS No. | 106-02-5 | Density | 0.885 g/cm3 |
| PSA | 26.30000 | LogP | 4.61450 |
| 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 | N/A | Appearance | white crystalline low melting solid |
| Safety | 24/25 | Risk Codes | N/A |
| Molecular Structure |
|
Hazard Symbols | N/A |
| 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; |
Article Data | 122 |
Cyclopentadecanolide Synthetic route
- 106-02-5
pentadecanolide
| 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 | 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 | 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 | 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 | 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 |
| 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 | 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 | Yield |
|---|---|
| dipropylboryl triflate In toluene Heating; | 94% |
- 106-02-5
pentadecanolide
| 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 | 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; |
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%.
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%.
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. |
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