Oleic Acid

Formula: C₁₈H₃₄O₂
Molecular weight: 282.4614
IUPAC Standard InChI: InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-
IUPAC Standard InChIKey: ZQPPMHVWECSIRJ-KTKRTIGZSA-N
CAS Registry Number: 112-80-1
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.
Stereoisomers:
- 9-Octadecenoic acid, (E)-
- 9-Octadecenoic acid
Other names: 9-Octadecenoic acid (Z)-; Δ9-cis-Oleic acid; cis-Oleic Acid; cis-9-Octadecenoic Acid; Emersol 211; Emersol 220 White Oleic Acid; Emersol 221 Low Titer White Oleic Acid; Oelsauere; Oleine 7503; Pamolyn 100; Vopcolene 27; Wecoline OO; Z-9-Octadecenoic acid; cis-Octadec-9-enoic acid; cis-Δ9-octadecenoic acid; cis-Δ9-Octadecenoate; neo-Fat 90-04; neo-Fat 92-04; Century cd fatty acid; Elaidoic acid; Emersol 210; Emersol 213; Emersol 6321; Glycon RO; Glycon WO; Groco 2; Groco 4; Groco 5l; Groco 6; Hy-phi 1055; Hy-phi 1088; Hy-phi 2066; Hy-phi 2088; Hy-phi 2102; K 52; L'Acide oleique; Metaupon; Tego-oleic 130; 9-Octadecenoic acid, cis-; Elaic acid; Industrene 105; Industrene 205; Industrene 206; Oleinic acid; Pamolyn; Wochem no. 320; (Z)-9-Octadecanoic acid; Emersol 6313 NF; Priolene 6906; 9-(Z)-octadecenoic acid; (Z)-Octadec-9-enoic acid; 9-Octadecenoic acid (9Z)-; D 100; Emersol 205; Extraolein 90
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Information on this page:
Other data available:
- Mass spectrum (electron ionization)
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NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Condensed phase thermochemistry data

Go To: Top, Phase change data, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, References, Notes

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_liquid	-764.8	kJ/mol	Chyd	Rogers, Hoyte, et al., 1978	Authors gave two values
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-11160.7	kJ/mol	Ccb	Keffler, 1930	At 293 °K; Corresponding Δ_fHº_liquid = -781.65 kJ/mol (simple calculation by NIST; no Washburn corrections)

Phase change data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, References, Notes

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
T_fus	289.45	K	N/A	Mod, Magne, et al., 1962	Uncertainty assigned by TRC = 0.3 K; TRC
T_fus	289.45	K	N/A	Mod, Magne, et al., 1960	Uncertainty assigned by TRC = 0.5 K; TRC

Reduced pressure boiling point

T_boil (K)	Pressure (bar)	Reference	Comment
467.7	0.001	Aldrich Chemical Company Inc., 1990	BS

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
83.8	456.	A	Stephenson and Malanowski, 1987	Based on data from 441. to 633. K.; AC

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)

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Temperature (K)	A	B	C	Reference	Comment
449.7 to 633.	5.04842	2555.604	-127.258	Stull, 1947	Coefficents calculated by NIST from author's data.

Enthalpy of fusion

Δ_fusH (kJ/mol)	Temperature (K)	Reference	Comment
39.6	286.5	Domalski and Hearing, 1996	AC

Enthalpy of phase transition

ΔH_trs (kJ/mol)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
39.600	286.45	crystaline, α	liquid	Sato, Yoshimoto, et al., 1990	High-melting, α-form.; DH
51.900	289.35	crystaline, β	liquid	Sato, Yoshimoto, et al., 1990	Low-melting, β-form.; DH

Entropy of phase transition

ΔS_trs (J/mol*K)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
138.4	286.45	crystaline, α	liquid	Sato, Yoshimoto, et al., 1990	High-melting,; DH
179.3	289.35	crystaline, β	liquid	Sato, Yoshimoto, et al., 1990	Low-melting,; DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

Reaction thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

Oleic Acid + =

By formula: C₁₈H₃₄O₂ + H₂ = C₁₈H₃₆O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-123.6 ± 1.6	kJ/mol	Chyd	Rogers, Hoyte, et al., 1978	liquid phase; solvent: Hexane; Authors gave two values
Δ_rH°	-125.1 ± 0.8	kJ/mol	Chyd	Rogers, Hoyte, et al., 1978	liquid phase; solvent: Hexane; Authors gave two values

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

LIQUID (NEAT); PERKIN-ELMER 180 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Chromatography

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, References, Notes

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	2140.	Asuming, Beauchamp, et al., 2005	30. m/0.25 mm/0.25 μm, He, 50. C @ 10. min, 3. K/min, 250. C @ 5. min
Capillary	SPB-1	2171.	Nagarajan, Rao, et al., 2001	30. m/0.32 mm/0.25 μm, He, 60. C @ 2. min, 2. K/min, 250. C @ 5. min

Kovats' RI, non-polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-5MS	2115.	Maia, Andrade, et al., 2000	30. m/0.25 mm/0.25 μm, He; Program: 40C => 2C/min => 60C => 4C/min => 260C
Capillary	DB-5	2097.	Andrade, Santos, et al., 1998	30. m/0.25 mm/0.25 μm, He; Program: 40C => 2C/min => 60C => 4C/min => 260C

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	2102.	Benkaci-Ali, Baaliouamer, et al., 2007	30. m/0.25 mm/0.25 μm, He, 60. C @ 8. min, 2. K/min, 250. C @ 30. min
Capillary	HP-5MS	2175.	Vujisic L., Vuckovic I., et al., 2006	30. m/0.25 mm/0.25 μm, H2, 4.3 K/min; T_start: 50. C; T_end: 285. C
Capillary	HP-5MS	2141.	Pino, Mesa, et al., 2005	30. m/0.25 mm/0.25 μm, He, 60. C @ 2. min, 4. K/min, 250. C @ 20. min
Capillary	SPB-5	2137.	Pino, Marbot, et al., 2003	30. m/0.25 mm/0.25 μm, He, 60. C @ 2. min, 4. K/min, 250. C @ 20. min
Capillary	HP-5	2152.	Skaltsa, Demetzos, et al., 2003	30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 4. K/min; T_end: 280. C
Capillary	HP-5	2141.	Flamini, Cioni, et al., 2002	30. m/0.25 mm/0.25 μm, N2, 60. C @ 10. min, 5. K/min; T_end: 220. C
Capillary	DB-5	2147.	Nogueira, Bittrich, et al., 2001	30. m/0.25 mm/0.25 μm, H2, 3. K/min; T_start: 60. C; T_end: 240. C
Capillary	HP-5MS	2152.	Skaltsa, Mavrommati, et al., 2001	30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 4. K/min; T_end: 280. C
Capillary	Ultra-1	2113.	Richmond and Pombo-Villar, 1998	25. m/0.32 mm/0.52 μm, He, 15. K/min, 320. C @ 10. min; T_start: 35. C

Van Den Dool and Kratz RI, non-polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	VF-5MS	2146.1	Tret'yakov, 2007	30. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C
Capillary	DB-5MS	2130.	Varlet V., Knockaert C., et al., 2006	30. m/0.32 mm/0.5 μm, He; Program: 70C(1min) => 3C/min => 80C(1min) => 5C/min => 150C => 10C/min => 280C (4min)

Van Den Dool and Kratz RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	3184.	Chung, Eiserich, et al., 1994	He, 60. C @ 4. min, 3. K/min, 220. C @ 30. min; Column length: 60. m; Column diameter: 0.25 mm
Capillary	DB-Wax	3173.	Shiratsuchi, Shimoda, et al., 1994	60. m/0.25 mm/0.25 μm, He, 2. K/min, 230. C @ 60. min; T_start: 50. C

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DP-5	2175.	Vijayakumar, Duraipandiyan, et al., 2012	30. m/0.25 mm/0.25 μm, Helium, 80. C @ 1. min, 4. K/min, 300. C @ 40. min
Capillary	DP-5	2175.	Vijayakumar, Duraipandiyan, et al., 2012	30. m/0.25 mm/0.25 μm, Helium, 80. C @ 1. min, 4. K/min, 300. C @ 40. min
Capillary	VF-5 MS	2131.	Liu, Lu, et al., 2011	30. m/0.25 mm/0.25 μm, Helium, 40. C @ 3. min, 5. K/min, 250. C @ 3. min
Capillary	DB-5 MS	2141.	Stojanovic, RAdulovic, et al., 2011	30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 290. C @ 10. min; T_start: 70. C
Capillary	HP-5 MS	2147.	Jerkovic, Hegic, et al., 2010	30. m/0.25 mm/0.25 μm, Helium, 70. C @ 2. min, 3. K/min, 200. C @ 18. min
Capillary	HP-5 MS	2147.	Jerkovic, Tuberso, et al., 2010	30. m/0.25 mm/0.25 μm, Helium, 70. C @ 2. min, 3. K/min, 200. C @ 18. min
Capillary	DB-1	2116.	Xu, Tang, et al., 2010	30. m/0.25 mm/0.25 μm, Helium, 50. C @ 2. min, 4. K/min, 220. C @ 2. min
Capillary	HP-5 MS	2146.	Radulovic, Blagojevic, et al., 2009	30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 290. C @ 10. min; T_start: 70. C
Capillary	HP-1	2090.	Wetwiayaklung, Thavanapong, et al., 2009	25. m/0.32 mm/0.17 μm, 50. C @ 5. min, 1. K/min, 260. C @ 5. min
Capillary	HP-101	2180.	Blazevic and Mastelic, 2008	25. m/0.20 mm/0.25 μm, Helium, 70. C @ 2. min, 3. K/min; T_end: 200. C
Capillary	HP-101	2180.	Blazevic and Mastelic, 2008	25. m/0.20 mm/0.25 μm, Helium, 70. C @ 2. min, 3. K/min; T_end: 200. C
Capillary	DB-5	2115.	Senatore, Landolfi, et al., 2006	30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 2. K/min, 260. C @ 20. min
Capillary	DB-5	2115.	Senatore, Apostolides Arnold, et al., 2005	30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 2. K/min, 260. C @ 20. min
Capillary	DB-5	2110.	Senatore, Rigano, et al., 2004	30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 2. K/min, 250. C @ 20. min
Capillary	DB-5	2161.	Priestap, van Baren, et al., 2003	30. m/0.2 mm/0.25 μm, He, 75. C @ 4. min, 3. K/min; T_end: 220. C
Capillary	DB-5	2112.	Palmeira, Conserva, et al., 2001	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 270. C
Capillary	DB-5	2115.	Palmeira, Conserva, et al., 2001	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 270. C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	VF-5 MS	2131.	Liu, Lu, et al., 2011	30. m/0.25 mm/0.25 μm, Helium; Program: not specified
Capillary	DB-1	2152.	Xu, Tang, et al., 2010	30. m/0.25 mm/0.25 μm, Helium; Program: not specified
Capillary	ZB-1 MS	2175.	Al-Reza, Rahman, et al., 2009	30. m/0.25 mm/0.25 μm, Helium; Program: 50 0C 3 0C/min -> 150 0C (10 min) 10 0C/min -> 250 0C
Capillary	HP-5 MS	2120.	Mancini, Arnold, et al., 2009	30. m/0.25 mm/0.25 μm, Helium; Program: 40 0C (5 min) 2 0C/min -> 270 0C -> 260 0C (20 min)
Capillary	RTX-5 MS	2173.	Mebazaa, Mahmoudi, et al., 2009	30. m/0.25 mm/0.25 μm, Helium; Program: 50 0C (5 min) 2 0C/min -> 100 0C (5 min) 5 0C/min -> 300 0C
Capillary	RTX-5 MS	2161.	Mebazaa, Mahmoudi, et al., 2009	30. m/0.25 mm/0.25 μm, Helium; Program: not specified
Capillary	HP-1	2098.	Wetwiayaklung, Thavanapong, et al., 2009	25. m/0.32 mm/0.17 μm; Program: not specified
Capillary	HP-5MS	2112.	Ning, Zheng, et al., 2008	30. m/0.25 mm/0.25 μm, He; Program: 40 0C (2 min) 3 0C/min -> 180 0C (2 min) 15 0C -> 280 0C
Capillary	HP-5	2146.	Zhao, Li, et al., 2008	30. m/0.25 mm/0.25 μm; Program: 40 0C (2 min) 5 0C/min -> 80 0C 7 oC/min -> 160 0C 9 0C/min -> 200 0C 20 0C/min -> 280 0C (10 min)
Capillary	HP-5	2141.	Zhao, Li, et al., 2008	30. m/0.25 mm/0.25 μm; Program: not specified
Capillary	HP-5MS	2155.	Alissandrakis, Kibaris, et al., 2005	30. m/0.25 mm/0.25 μm, He; Program: 40C(3min) => 2C/min => 180C => 10C/min => 250C(5min)

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	3172.	Guo, Wu, et al., 2008	30. m/0.25 mm/0.25 μm, Helium, 60. C @ 2. min, 10. K/min, 250. C @ 10. min
Capillary	TC-WAX FFS	3142.	Miyazawa, Maehara, et al., 2002	He, 3. K/min; Column length: 60. m; Column diameter: 0.25 mm; T_start: 60. C; T_end: 240. C
Capillary	TC-Wax	3150.	Miyazawa, Kurose, et al., 2001	He, 4. K/min, 250. C @ 47. min; Column length: 60. m; Column diameter: 0.25 mm; T_start: 80. C

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Innowax	3157.	Noorizadeh, Farmany, et al., 2011	60. m/0.25 mm/0.33 μm; Program: not specified
Capillary	HP Innowax	3157.	Mancini, Arnold, et al., 2009	50. m/0.20 mm/0.25 μm, Helium; Program: 40 0C (5 min) 2 0C/min -> 270 0C -> 260 0C (20 min)
Capillary	DB-FFAP	3184.	Mebazaa, Mahmoudi, et al., 2009	30. m/0.25 mm/0.25 μm, Helium; Program: not specified
Capillary	Innowax FSC	3200.	Baser, Özek, et al., 2004	60. m/0.25 mm/0.25 μm, He; Program: 60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, Notes

Rogers, Hoyte, et al., 1978
Rogers, D.W.; Hoyte, O.P.A.; Ho, R.K.C., Heats of hydrogenation of large molecules. Part 2. Six unsaturated and polyunsaturated fatty acids, J. Chem. Soc. Faraday Trans. 1, 1978, 74, 46-52. [all data]

Keffler, 1930
Keffler, L.J.P., Calorimetric researches on geometrical isomerism. Part I. Preliminary studies on oleic and elaidic acids and esters from a comparison of their heats of combustion, J. Phys. Chem., 1930, 34, 1319-1325. [all data]

Mod, Magne, et al., 1962
Mod, R.R.; Magne, F.C.; Skau, E.L., J. Chem. Eng. Data, 1962, 7, 31. [all data]

Mod, Magne, et al., 1960
Mod, R.R.; Magne, F.C.; Skau, E.L., Pure Acid-Free Amides of C18 Fatty Acids. Their Preparation and Binary Freezing Point Behavior, J. Chem. Eng. Data, 1960, 5, 478. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Sato, Yoshimoto, et al., 1990
Sato, K.; Yoshimoto, N.; Suzuki, M.; Kobayashi, M.; Kaneko, F., Structure and transformation in polymorphism of petroselinic acid (cis-w-12-octadecenoic acid), J. Phys. Chem., 1990, 94, 3180-3185. [all data]

Asuming, Beauchamp, et al., 2005
Asuming, W.A.; Beauchamp, P.S.; Descalzo, J.T.; Dev, B.C.; Dev, V.; Frost, S.; Ma, C.W., Essential oil composition of four Lomatium Raf. species and their chemotaxonomy, Biochem. Syst. Ecol., 2005, 33, 1, 17-26, https://doi.org/10.1016/j.bse.2004.06.005 . [all data]

Nagarajan, Rao, et al., 2001
Nagarajan, S.; Rao, L.J.M.; Guirudutt, K.N., Chemical composition of the volatiles of Decalepis hamiltonii (Wight Arn), Flavour Fragr. J., 2001, 16, 1, 27-29, https://doi.org/10.1002/1099-1026(200101/02)16:1<27::AID-FFJ937>3.0.CO;2-F . [all data]

Maia, Andrade, et al., 2000
Maia, J.G.S.; Andrade, E.H.A.; Zoghbi, M.G.B., Volatile constituents of the leaves, fruits and flowers of cashew ( Anacardium occidentaleL.), J. Food Comp. Anal., 2000, 13, 3, 227-232, https://doi.org/10.1006/jfca.2000.0894 . [all data]

Andrade, Santos, et al., 1998
Andrade, E.H.A.; Santos, A.S.; Zoghbi, M.G.B.; Maia, J.G.S., Volatile constituents of fruits of Astrocarium vulgare Mart. and Bactris gasipaes H.B.K. (Arecaceae), Flavour Fragr. J., 1998, 13, 3, 151-153, https://doi.org/10.1002/(SICI)1099-1026(199805/06)13:3<151::AID-FFJ712>3.0.CO;2-E . [all data]

Benkaci-Ali, Baaliouamer, et al., 2007
Benkaci-Ali, F.; Baaliouamer, A.; Meklati, B.Y.; Chemat, F., Chemical composition of seed essential oils from Algerian Nigella sativa extracted by microwave and hydrodistillation, Flavour Fragr. J., 2007, 22, 2, 148-153, https://doi.org/10.1002/ffj.1773 . [all data]

Vujisic L., Vuckovic I., et al., 2006
Vujisic L.; Vuckovic I.; Tesevic V.; Dokovic D.; Ristic M.S.; Janackovic P.; Milosavljevic S., Comparative examination of the essential oils of Anthemis ruthenica and A-arvensis wild-growing in Serbia, Flavour Fragr. J., 2006, 21, 3, 458-461, https://doi.org/10.1002/ffj.1681 . [all data]

Pino, Mesa, et al., 2005
Pino, J.A.; Mesa, J.; Muñoz, Y.; Martí, M.P.; Marbot, R., Volatile components from mango (Mangifera indica L.) cultivars, J. Agric. Food Chem., 2005, 53, 6, 2213-2223, https://doi.org/10.1021/jf0402633 . [all data]

Pino, Marbot, et al., 2003
Pino, J.; Marbot, R.; Rosado, A.; Vázquez, C., Volatile constituents of fruits of Garcinia dulcis Kurz. from Cuba, Flavour Fragr. J., 2003, 18, 4, 271-274, https://doi.org/10.1002/ffj.1187 . [all data]

Skaltsa, Demetzos, et al., 2003
Skaltsa, H.D.; Demetzos, C.; Lazari, D.; Sokovic, M., Essential oil analysis and antimicrobial activity of eight Stachys species from Greece, Phytochemistry, 2003, 64, 3, 743-752, https://doi.org/10.1016/S0031-9422(03)00386-8 . [all data]

Flamini, Cioni, et al., 2002
Flamini, G.; Cioni, P.L.; Morelli, I., Differences in the fragrances of pollen and different floral parts of male and female flowers of Laurus nobilis, J. Agric. Food Chem., 2002, 50, 16, 4647-4652, https://doi.org/10.1021/jf020269x . [all data]

Nogueira, Bittrich, et al., 2001
Nogueira, P.C.L.; Bittrich, V.; Shepherd, G.J.; Lopes, A.V.; Marsaioli, A.J., The ecological and taxonomic importance of flower volatiles of Clusia species (Guttiferae), Phytochemistry, 2001, 56, 5, 443-452, https://doi.org/10.1016/S0031-9422(00)00213-2 . [all data]

Skaltsa, Mavrommati, et al., 2001
Skaltsa, H.D.; Mavrommati, A.; Constantinidis, T., A chemotaxonomic investigation of volatile constituents in Stachys subsect. Swainsonianeae (Labiatae), Phytochemistry, 2001, 57, 2, 235-244, https://doi.org/10.1016/S0031-9422(01)00003-6 . [all data]

Richmond and Pombo-Villar, 1998
Richmond, R.; Pombo-Villar, E., Short communication. Use of persistent trace gas chromatography artifacts for the calculation of pseudo-Sadtler retention indices, J. Chromatogr. A, 1998, 811, 1-2, 241-245, https://doi.org/10.1016/S0021-9673(98)00285-4 . [all data]

Tret'yakov, 2007
Tret'yakov, K.V., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [all data]

Varlet V., Knockaert C., et al., 2006
Varlet V.; Knockaert C.; Prost C.; Serot T., Comparison of odor-active volatile compounds of fresh and smoked salmon, J. Agric. Food Chem., 2006, 54, 9, 3391-3401, https://doi.org/10.1021/jf053001p . [all data]

Chung, Eiserich, et al., 1994
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Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, References

Symbols used in this document:

T_boil	Boiling point
T_fus	Fusion (melting) point
ΔH_trs	Enthalpy of phase transition
ΔS_trs	Entropy of phase transition
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_fusH	Enthalpy of fusion
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_vapH	Enthalpy of vaporization

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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