Oxacyclohexadecan-2-one
- Formula: C15H28O2
- Molecular weight: 240.3816
- IUPAC Standard InChI: InChI=1S/C15H28O2/c16-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-17-15/h1-14H2
- IUPAC Standard InChIKey: FKUPPRZPSYCDRS-UHFFFAOYSA-N
- CAS Registry Number: 106-02-5
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Cyclopentadecanolide; Exaltolide; Muskalactone; Muskolactone; Pentadecalactone; Pentadecanoic acid, 15-hydroxy-, ξ-lactone; Pentadecanolide; Thibetolide; 1,15-Pentadecanolide; 15-Hydroxypentadecanoic acid, lactone; 2-Pentadecalone; Cyclopentadecanolactone; 15-Pentadecanolide; 15-Pentadecanolactone; Pentadecanolactone; Pentadecan-15-olide; Pentadecano-15-lactone; Pentalide; NSC 36763
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Condensed phase thermochemistry data
Go To: Top, Phase change data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -709. ± 4. | kJ/mol | Ccb | Yevstropov, Lebedev, et al., 1983 | ALS |
| ΔfH°solid | -725.5 ± 9.0 | kJ/mol | Ccb | Lebedev, Yevstropov, et al., 1981 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -9196. ± 4. | kJ/mol | Ccb | Yevstropov, Lebedev, et al., 1983 | Corresponding ΔfHºsolid = -708. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -9178.1 ± 8.8 | kJ/mol | Ccb | Lebedev, Yevstropov, et al., 1981 | Corresponding ΔfHºsolid = -726.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°solid,1 bar | 482.9 | J/mol*K | N/A | Yevstropov, Lebedev, et al., 1983, 2 | DH |
| S°solid,1 bar | 482.8 | J/mol*K | N/A | Lebedev, Yevstropov, et al., 1981, 2 | DH |
Constant pressure heat capacity of solid
| Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 444.6 | 298.15 | Yevstropov, Lebedev, et al., 1983, 2 | T = 5 to 330 K.; DH |
| 444.3 | 298.15 | Lebedev, Yevstropov, et al., 1981, 2 | T = 13.8 to 330 K.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tfus | 310.2 | K | N/A | Voitkevich and Lyubshits, 1957 | Uncertainty assigned by TRC = 1. K; TRC |
| Tfus | 310.15 | K | N/A | Serpinskii, Voitkevich, et al., 1954 | Uncertainty assigned by TRC = 0.6 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Ttriple | 308.5 | K | N/A | Evstropov, Lebedev, et al., 1983 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.1 K; TRC |
| Ttriple | 308.5 | K | N/A | Lebedev, Evstropov, et al., 1981 | Crystal phase 1 phase; Uncertainty assigned by TRC = 1. K; TRC |
| Ttriple | 308.5 | K | N/A | Lebedev, Evstropov, et al., 1979 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.1 K; TRC |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 78.2 | 378. | A | Stephenson and Malanowski, 1987 | Based on data from 363. - 443. K.; AC |
| 74.2 | 315. | A,ME | Stephenson and Malanowski, 1987 | Based on data from 310. - 320. K. See also Serpinskii, Voitkevich, et al., 1954, 2.; AC |
Enthalpy of sublimation
| ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 81.3 | 300. | ME | Stephenson and Malanowski, 1987 | Based on data from 290. - 310. K. See also Jones, 1960 and Serpinskii, Voitkevich, et al., 1954, 2.; AC |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 6.99 | 308.5 | AC | Pitzer, Peiper, et al., 1984 | Based on data from 10. - 370. K. See also Lebedev, Yevstropov, et al., 1981.; AC |
Entropy of fusion
| ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 96.47 | 283. | Domalski, Evans, et al., 1984 | CAL |
| 22.65 | 308.5 |
Enthalpy of phase transition
| ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
|---|---|---|---|---|---|
| 27.300 | 282.98 | crystaline, II | crystaline, I | Yevstropov, Lebedev, et al., 1983, 2 | DH |
| 6.980 | 308.5 | crystaline, I | liquid | Yevstropov, Lebedev, et al., 1983, 2 | DH |
| 0. | 193. | crystaline, I'' | crystaline, I' | Yevstropov, Lebedev, et al., 1983, 2 | DH |
| 27.301 | 282.98 | crystaline, II | crystaline, I | Lebedev, Yevstropov, et al., 1981, 2 | DH |
| 6.979 | 308.5 | crystaline, I | liquid | Lebedev, Yevstropov, et al., 1981, 2 | DH |
Entropy of phase transition
| ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
|---|---|---|---|---|---|
| 96.3 | 282.98 | crystaline, II | crystaline, I | Yevstropov, Lebedev, et al., 1983, 2 | DH |
| 22.6 | 308.5 | crystaline, I | liquid | Yevstropov, Lebedev, et al., 1983, 2 | DH |
| 0. | 193. | crystaline, I'' | crystaline, I' | Yevstropov, Lebedev, et al., 1983, 2 | DH |
| 96.2 | 282.98 | crystaline, II | crystaline, I | Lebedev, Yevstropov, et al., 1981, 2 | DH |
| 22.6 | 308.5 | crystaline, I | liquid | Lebedev, Yevstropov, et al., 1981, 2 | DH |
IR Spectrum
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Additional Data
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| Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| Origin | Sadtler Research Labs Under US-EPA Contract |
| State | gas |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Gas Chromatography, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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| Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| Origin | Japan AIST/NIMC Database- Spectrum MS-NW-7026 |
| NIST MS number | 236668 |
Gas Chromatography
Go To: Top, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | SE-30 | 100. | 1840.6 | Tudor, 1997 | 40. m/0.35 mm/0.35 μm |
Kovats' RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5 | 1828. | Lopes, Strobl, et al., 2004 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 60. C; Tend: 260. C |
| Capillary | DB-5 | 1806. | Marongiu, Piras, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 3. K/min, 240. C @ 30. min; Tstart: 60. C |
Kovats' RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-Wax | 2233. | Lopes, Strobl, et al., 2004 | 30. m/0.32 mm/0.25 μm, He, 40. C @ 5. min, 3. K/min; Tend: 220. C |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5 MS | 1839. | Radulovic, Blagojevic, et al., 2010 | 30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 290. C @ 10. min; Tstart: 70. C |
| Capillary | CP Sil 5 CB | 1839. | Jassbi, Mehrdad, et al., 2005 | 30. m/0.25 mm/0.25 μm, N2, 5. K/min, 250. C @ 10. min; Tstart: 60. C |
| Capillary | DB-1 | 1821. | Khanavi, Ghasemian, et al., 2005 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 1. min, 2.5 K/min, 265. C @ 20. min |
| Capillary | HP-5MS | 1823. | Malencic, Couladis, et al., 2004 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 60. C; Tend: 280. C |
| Capillary | Optima-1 | 1846. | de Beck, Bessière, et al., 2000 | 25. m/0.20 mm/0.25 μm, He, 50. C @ 3. min, 3. K/min; Tend: 250. C |
| Capillary | SPB-5 | 1844. | Doneanu and Anitescu, 1998 | 50. m/0.32 mm/0.25 μm, He, 3. K/min, 240. C @ 20. min; Tstart: 60. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | CP Sil 8 CB | 1834. | Butkienë, Nivinskienë, et al., 2005 | 50. m/0.32 mm/0.25 μm, He; Program: 50C(5min) => 2C/min => 90C => 15C/min => 240C(4min) |
| Capillary | CP Sil 8 CB | 1828. | Nivinskienë, Butkienë, et al., 2005 | 50. m/0.32 mm/0.25 μm, He; Program: 60C(1min) => 5C/min => 160C => 5C/min => 250C(3min) |
| Capillary | CP Sil 8 CB | 1834. | Butkienë, Nivinskienë, et al., 2004 | 50. m/0.32 mm/0.25 μm, He; Program: 50C(5min) => 2C/min => 90C => 15C/min => 240C(4min) |
| Capillary | SE-30 | 1823. | Vinogradov, 2004 | Program: not specified |
Normal alkane RI, polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Carbowax 20M | 2255. | Vinogradov, 2004 | Program: not specified |
| Capillary | NB-351 | 2242. | Kerrola and Kallio, 1994 | 25. m/0.32 mm/0.2 μm, He; Program: 35C(5min) => 2.5C/min => 150C => 5C/min => 240C (20min) |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Yevstropov, Lebedev, et al., 1983
Yevstropov, A.A.; Lebedev, B.V.; Kiparisova, Ye.G.,
Thermodynamics of pentadecanolactone, of the process of its polymerization and of the resultant polypentadecanolactone in the 0-400 K region,
Polym. Sci. USSR, 1983, 25, 1951-1959. [all data]
Lebedev, Yevstropov, et al., 1981
Lebedev, B.V.; Yevstropov, A.A.; Kiparisova, Ye.G.,
Thermodynamics of undecanolactone, tridecanolactone, and pentadecanolactone from 0 to 340 K,
J. Chem. Thermodyn., 1981, 13, 1185-1204. [all data]
Yevstropov, Lebedev, et al., 1983, 2
Yevstropov, A.A.; Lebedev, B.V.; Krparisova, Ye.G.,
Thermodynamics of pentadecanolactone, of the process of its polymerization and of the resultant polypentadecanolactone in the 0 to 400 K region, Vysokomol. Soedin,
Ser., 1983, A 25(8), 1679-1685. [all data]
Lebedev, Yevstropov, et al., 1981, 2
Lebedev, B.V.; Yevstropov, A.A.; Kiparisova, Y.G.,
Thermodynamic properties of undecanolactone over the range, 1981, Termodin. [all data]
Voitkevich and Lyubshits, 1957
Voitkevich, S.A.; Lyubshits, N.Yu.,
Maslob-Zhir. Prom-st., 1957, No. 4, 20. [all data]
Serpinskii, Voitkevich, et al., 1954
Serpinskii, V.V.; Voitkevich, S.A.; Lyuboshits, N.Y.,
Zh. Fiz. Khim., 1954, 28, 1969. [all data]
Evstropov, Lebedev, et al., 1983
Evstropov, A.A.; Lebedev, B.V.; Kiparisova, E.G.,
Thermodynamics of pentadecanolactone, its polymerization, and the resulting polypentadecanolactone in the 0-400 K region,
Vysokomol. Soedin., Ser. A, 1983, 25, 1679-1685. [all data]
Lebedev, Evstropov, et al., 1981
Lebedev, B.V.; Evstropov, A.A.; Kiparisova, Ye.G.,
Thermodynamics of undecanolactone, tridecanolactone, and pentadecanolactone from 0 to 340 K,
J. Chem. Thermodyn., 1981, 13, 1185. [all data]
Lebedev, Evstropov, et al., 1979
Lebedev, B.V.; Evstropov, A.A.; Shurygina, A.M.,
Heat capacity and thermodynamic properties of pentadecanolactone in the O-3 30 K range,
Termodin. Org. Soedin. (USSR), 1979, 1979, 5. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Serpinskii, Voitkevich, et al., 1954, 2
Serpinskii, V.V.; Voitkevich, S.A.; Lyuboshits, N.Y.,
Zh. Fiz. Khim., 1954, 28, 810. [all data]
Jones, 1960
Jones, A.H.,
Sublimation Pressure Data for Organic Compounds.,
J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019
. [all data]
Pitzer, Peiper, et al., 1984
Pitzer, Kenneth S.; Peiper, J. Christopher; Busey, R.H.,
Thermodynamic Properties of Aqueous Sodium Chloride Solutions,
J. Phys. Chem. Ref. Data, 1984, 13, 1, 1, https://doi.org/10.1063/1.555709
. [all data]
Domalski, Evans, et al., 1984
Domalski, E.S.; Evans, W.H.; Hearing, E.D.,
J. Phys. Chem. Ref. Data, suppl. 1, 1984. [all data]
Tudor, 1997
Tudor, E.,
Temperature dependence of the retention index for perfumery compounds on a SE-30 glass capillary column. I. Linear equations,
J. Chromatogr. A, 1997, 779, 1-2, 287-297, https://doi.org/10.1016/S0021-9673(97)00453-6
. [all data]
Lopes, Strobl, et al., 2004
Lopes, D.; Strobl, H.; Kolodziejczyk, P.,
14-Methylpentadecano-15-lactone (Muscolide): a new macrocyclic lactone from the oil of Angelica archangelica L.,
Chemistry and Biodiversity, 2004, 1, 12, 1880-1887, https://doi.org/10.1002/cbdv.200490144
. [all data]
Marongiu, Piras, et al., 2003
Marongiu, B.; Piras, A.; Pani, F.; Porcedda, S.; Ballero, M.,
Extraction, separation and isolation of essential oils from natural matrices by supercritical CO2,
Flavour Fragr. J., 2003, 18, 6, 505-509, https://doi.org/10.1002/ffj.1258
. [all data]
Radulovic, Blagojevic, et al., 2010
Radulovic, N.; Blagojevic, P.; Palic, R.,
Comparative study of the leaf volatiles of Arctostaphylos uva-ursi (L.) Spreng. and Vaccinium vitis-idaea L. (Ericaceae),
Molecules, 2010, 15, 9, 6168-6185, https://doi.org/10.3390/molecules15096168
. [all data]
Jassbi, Mehrdad, et al., 2005
Jassbi, A.R.; Mehrdad, M.; Soleimani, M.; Mirzaeian, M.; Sonboli, A.,
Chemical composition of the essential oils of Bunium elegans and Bunium caroides,
Chem. Nat. Compd. (Engl. Transl.), 2005, 41, 4, 415-417, https://doi.org/10.1007/s10600-005-0165-0
. [all data]
Khanavi, Ghasemian, et al., 2005
Khanavi, M.; Ghasemian, L.; Motlagh, E.H.; Hadjiakhoondi, A.; Shafiee, A.,
Chemical composition of the essential oils of Marrubium parviflorum Fisch. C.A. Mey. and Marrubium vulgare L. from Iran,
Flavour Fragr. J., 2005, 20, 3, 324-326, https://doi.org/10.1002/ffj.1425
. [all data]
Malencic, Couladis, et al., 2004
Malencic, Dj.; Couladis, M.; Mimica-Dukic, N.; Popovic, M.; Boza, P.,
Essential oils of three Salvia species from the Pannonian part of Serbia,
Flavour Fragr. J., 2004, 19, 3, 225-228, https://doi.org/10.1002/ffj.1291
. [all data]
de Beck, Bessière, et al., 2000
de Beck, P.O.; Bessière, J.M.; Dijoux-Franca, M.-G.; David, B.; Mariotte, A.-M.,
Volatile constituents from leaves and wood of Leea guineensis G. Don (Leeaceae) from Cameroon,
Flavour Fragr. J., 2000, 15, 3, 182-185, https://doi.org/10.1002/1099-1026(200005/06)15:3<182::AID-FFJ888>3.0.CO;2-X
. [all data]
Doneanu and Anitescu, 1998
Doneanu, C.; Anitescu, G.,
Supercritical carbon dioxide extraction of Angelica archangelica L. root oil,
J. Supercrit. Fluids, 1998, 12, 1, 59-67, https://doi.org/10.1016/S0896-8446(97)00040-5
. [all data]
Butkienë, Nivinskienë, et al., 2005
Butkienë, R.; Nivinskienë, O.; Mockutë, D.,
α-Pinene chemotype of leaf (needle) essential oils of Juniperus communis L. growing wild in Vilnius district,
Chemija, 2005, 16, 1, 53-60. [all data]
Nivinskienë, Butkienë, et al., 2005
Nivinskienë, O.; Butkienë, R.; Mockutë, D.,
Chemical composition of seed (fruit) essential oils of Angelica archangelica L. growing wild in Lithuania,
Chemija, 2005, 16, 3-4, 51-54. [all data]
Butkienë, Nivinskienë, et al., 2004
Butkienë, R.; Nivinskienë, O.; Mockutë, D.,
Chemical composition of unripe and ripe berry essential oils of Juniperus communis L. growing wild in Vilnius district,
Chemija, 2004, 15, 4, 57-63. [all data]
Vinogradov, 2004
Vinogradov, B.A.,
Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]
Kerrola and Kallio, 1994
Kerrola, K.M.; Kallio, H.P.,
Extraction of volatile compounds of angelica (Angelica archangelica L.) root by liquid carbon dioxide,
J. Agric. Food Chem., 1994, 42, 10, 2235-2245, https://doi.org/10.1021/jf00046a030
. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH Enthalpy of sublimation ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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