Phytol

Formula: C₂₀H₄₀O
Molecular weight: 296.5310
IUPAC Standard InChI: InChI=1S/C20H40O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h15,17-19,21H,6-14,16H2,1-5H3/b20-15+/t18-,19-/m0/s1
IUPAC Standard InChIKey: BOTWFXYSPFMFNR-PFIWFTBQSA-N
CAS Registry Number: 150-86-7
Chemical structure:
This structure is also available as a 2d Mol file
Stereoisomers:
- 3,7,11,15-Tetramethyl-2-hexadecen-1-ol
- cis-Phytol
Other names: 2-Hexadecen-1-ol, 3,7,11,15-tetramethyl-, [R-[R*,R*-(E)]]-; trans-Phytol; 3,7,11,15-Tetramethyl-2-hexadecen-1-ol-, (2E,7R,11R)-; (2E,7R,11R)-3,7,11,15-Tetramethyl-2-hexadecen-1-ol; 3,7,11,15-teramethyl-2-hexadecene-1-ol-, (2E,7R,11R)-; (E)-Phytol; 5016-81-9; 3,7,11,15-Tetramethyl-2-hexadecen-1-ol; 3,7,11,15-teramethyl-2-hexadecene-1-ol; 3,7,11,15-tetramethylhexadec-2-en-1-ol
Permanent link for this species. Use this link for bookmarking this species for future reference.
Information on this page:
Other data available:
- Mass spectrum (electron ionization)
- Gas Chromatography
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Normal alkane RI, polar column, custom temperature program

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

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Innowax FSC	Innowax FSC	Innowax FSC	Innowax FSC	HP Innowax
Column length (m)	60.	60.	60.	60.	50.
Carrier gas	Helium	Helium	Helium	Helium	Helium
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.20
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
Program	60 0C (10 min) 4 0C/min -> 220 0C (10 min) 1 oC/min -> 240 0C	60 0C (10 min) 4 0C/min -> 220 0C 1 0C/min -> 240 0C	60 0C (10 min) 4 0C/min -> 220 0C (10 min) 1 0C/min -> 240 0C	60 0C (10 min) 4 0C/min -> 220 0C (10 min) 1 0C/min -> 240 0C	40 0C (5 min) 2 0C/min -> 270 0C -> 260 0C (20 min)
I	2622.	2622.	2622.	2622.	2622.
Reference	Akin, Saracoglu, et al., 2012	Bardakci, Demirci, et al., 2012	Polatoglu, Demirci, et al., 2010	Baser, Demirci, et al., 2009	Mancini, Arnold, et al., 2009
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-Innowax FSC	HP-Innowax	Innowax FSC	Carbowax 20M	HP-Innowax FSC
Column length (m)	60.	50.	60.	30.	60.
Carrier gas	N2	He	Nitrogen	He	He
Substrate
Column diameter (mm)	0.25	0.2	0.25		0.25
Phase thickness (μm)	0.25	0.2	0.25		0.25
Program	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	40C(5min) => 2C/min => 250C(15min) => 10C/min => 270C	60 0C (10 min) 1 0C/min -> 220 0C (10 min) 1 0C/min -> 240 0C	60C(5min) => 3C/min => 180C => 20C/min => 280C(10min)	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C
I	2622.	2622.	2622.	2615.	2622.
Reference	Baser K.H.C. and Demirci B., 2007	Formisano, Mignola, et al., 2007	Kaya, Benirci, et al., 2007	Merle, Verdeguer, et al., 2007	Tabanca N., Demirci B., et al., 2007
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP Innowax FSP	Innowax FSC	Innowax FSC	HP-Innowax FSC	HP-Innowax FSC
Column length (m)	60.	60.	60.	60.	60.
Carrier gas	N2	He	He	N2	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
Program	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min >220C (10min) => 1C/min => 240C	60C(10min) => 4C/min >220C (10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C (10min) => 1C/min => 240C
I	2622.	2622.	2622.	2622.	2622.
Reference	Tabanca N., Demirci B., et al., 2007, 2	Baser, Özek, et al., 2006	Baser, Özek, et al., 2006	Demirci B., Baser K.H.C., et al., 2006	Kürkçüoglu, Hüsnü Can Baser, et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-Innowax	HP-Innowax FSC	HP-Innowax FSC	HP-Innowax	HP Innowax FSP
Column length (m)	50.	60.	60.	60.	60.
Carrier gas	He	He		N2	N2
Substrate
Column diameter (mm)	0.2	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.2	0.25	0.25	0.25	0.25
Program	40C(5min) => 2C/min => 250C (15min) => 10C/min => 270C	60(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C (10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C
I	2622.	2622.	2622.	2622.	2622.
Reference	Senatore, Apostolides Arnold, et al., 2006	Suleimenov Y.M., Atazhanova G.A., et al., 2006	Tabanca, Demirci, et al., 2006	Duman, Kartal, et al., 2005	Altintas, Kose, et al., 2004
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Innowax FSC	HP-Innowax FSC	HP-Innowax	HP-Innowax FSC	Innowax FSC
Column length (m)	60.	60.	50.	60.	60.
Carrier gas	He	He		He	He
Substrate
Column diameter (mm)	0.25	0.25	0.2	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.2	0.25	0.25
Program	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	not specified	60C (10min) => 4C/min => 220C (10min) => 1C/min => 240C	60C (10min) => 4C/min => 220C (10min) => 1C/min => 240C
I	2622.	2622.	2622.	2622.	2622.
Reference	Baser, Özek, et al., 2004	Kivcak, Akay, et al., 2004	Senatore, Apostolides Arnold, et al., 2004	Demirci, Baser, et al., 2003	Demirci and Baser, 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-Innowax FSC	HP-Innowax FSC	HP-Innowax FSC	HP-Innowax FSC	HP-Innowax
Column length (m)	60.	60.	60.	60.	60.
Carrier gas	He	He	He	N2	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
Program	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60 0C (10 min) 10 K/min -> 220 0C (10 min) 1K/min -> 240 0C
I	2622.	2622.	2622.	2622.	2622.
Reference	Demirci, Dadandi, et al., 2003	Demirci, Demirci, et al., 2003	Erdemoglu, Sener, et al., 2003	Hüsnü Can Baser, Demirci, et al., 2002	Baser, Demirci, et al., 2001
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-Innowax FSC	HP-Innowax FSC	Innowax	HP-Innowax	Innowax FSC
Column length (m)	60.	60.	60.	60.	60.
Carrier gas		He	He	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
Program	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 200C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10 min) => 4C/min => 220C(10min) => 1C/min => 240C
I	2622.	2622.	2622.	2622.	2622.
Reference	Kaya, Demirci, et al., 2001	Kirimer N., Tabanea N., et al., 2001	Özcan, Akgül, et al., 2001	Tabanca, Kirimer, et al., 2001	Kirimer, Tabanca, et al., 2000
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary
Active phase	Innowax FSC	Innowax
Column length (m)	60.	60.
Carrier gas	Helium
Substrate
Column diameter (mm)	0.25	0.25
Phase thickness (μm)	0.25	0.25
Program	60 0C (10 min) 4 0C/min -> 220 0C (10 min) 1 0C/min -> 240 0C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C
I	2622.	2622.
Reference	Kirimer, Tabanca, et al., 1999	Baser, Kürkcüoglu, et al., 1998
Comment	MSDC-RI	MSDC-RI

References

Go To: Top, Normal alkane RI, polar column, custom temperature program, Notes

Akin, Saracoglu, et al., 2012
Akin, M.; Saracoglu, H.T.; Demirci, B.; Baser, K.H.C., Chemical composition and antibacterial activity of essential oils from different parts of Buplerum rotundifolium L., Rec. Nat. Prod., 2012, 6, 3, 316-320. [all data]

Bardakci, Demirci, et al., 2012
Bardakci, H.; Demirci, B.; Yesilada, E.; Kirmizibekmez, H.; Naser, K.H.C., Chemical composition of the essential oil of the subterranean parts of Valeriana alliariifolia, Rec. Nat. Prod., 2012, 6, 1, 89-92. [all data]

Polatoglu, Demirci, et al., 2010
Polatoglu, K.; Demirci, F.; Demirci, B.; Goren, N.; Baser, K.H.C., Antimicrobial activity and essential oil composition of a new T. argyrophyllum (C. Koch) Tvzel var. argyrophyllium chemotype, J. Oleo Sci., 2010, 59, 6, 307-313, https://doi.org/10.5650/jos.59.307 . [all data]

Baser, Demirci, et al., 2009
Baser, K.H.C.; Demirci, B.; Kurkcuoglu, M.; Satin, F.; Tumen, G., Comparative morphological and phytochemical charactertization of Salvia cadmica and S. smyrnaea, Pak. J. Bot., 2009, 41, 4, 1545-1555. [all data]

Mancini, Arnold, et al., 2009
Mancini, E.; Arnold, N.A.; De Martino, L.; De Feo, V.; Formisano, C.; Rigano, D.; Senatore, F., Chemical composition and phytotoxic effects of essential oils of Salvia hierosolymitana Boiss. and Salvia multicaulis Vahl. var. simplicifolia Boiss. growing wild in Lebanon, Molecules, 2009, 14, 11, 4725-4736, https://doi.org/10.3390/molecules14114725 . [all data]

Baser K.H.C. and Demirci B., 2007
Baser K.H.C.; Demirci B., Studies on Betula essential oils, Arkivoc, 2007, 7, 335-348. [all data]

Formisano, Mignola, et al., 2007
Formisano, C.; Mignola, E.; Rigano, D.; Senatore, F.; Bellone, G.; Bruno, M.; Rosselli, S., Chemical composition and antimicrobial activity of the essential oil from aerial parts of Micromeria fruticulosa (Bertol.) Grande (Lamiaceae) growing wild in Southern Italy, Flavour Fragr. J., 2007, 22, 4, 289-292, https://doi.org/10.1002/ffj.1795 . [all data]

Kaya, Benirci, et al., 2007
Kaya, A.; Benirci, B.; Baser, K.H.C., Micromorphology of glandular trichomes of Nepeta congesta Fisch. Mey. var. congesta (LAmiaceae) and chemical analysis of the essential oils, South African J. Botany, 2007, 73, 1, 29-34, https://doi.org/10.1016/j.sajb.2006.05.004 . [all data]

Merle, Verdeguer, et al., 2007
Merle, H.; Verdeguer, M.; Blázquez, M.A.; Boira, H., Chemical composition of the essential oils from Eriocephalus africanus L. var. africanus populations growing in Spain, Flavour Fragr. J., 2007, 22, 6, 461-464, https://doi.org/10.1002/ffj.1821 . [all data]

Tabanca N., Demirci B., et al., 2007
Tabanca N.; Demirci B.; Baser K.H.C.; Mincsovics E.; Khan S.I.; Jacob M.R.; Wedge D.E., Characterization of volatile constituents of Scaligeria tripartita and studies on the antifungal activity against phytopathogenic fungi, J. Chromatogr. B, 2007, 850, 1-2, 221-229, https://doi.org/10.1016/j.jchromb.2006.11.041 . [all data]

Tabanca N., Demirci B., et al., 2007, 2
Tabanca N.; Demirci B.; Crockett S.L.; Baser K.H.C.; Wedge D.E., Chemical composition and antifungal activity of Arnica longifolia, Aster hesperius, and Chrysothamnus nauseosus essential oils, J. Agric. Food Chem., 2007, 55, 21, 8430-8435, https://doi.org/10.1021/jf071379c . [all data]

Baser, Özek, et al., 2006
Baser, K.H.C.; Özek, G.; Özek, T.; Duran, A.; Duman, H., Composition of the essential oils of Rhabdosciadium oligocarpum (Post ex Boiss.) Hedge et Lamond and Rhabdosciadium microcalycinum Hand.-Mazz., Flavour Fragr. J., 2006, 21, 4, 650-655, https://doi.org/10.1002/ffj.1639 . [all data]

Demirci B., Baser K.H.C., et al., 2006
Demirci B.; Baser K.H.C.; Tabanca N.; Wedge D.E., Characterization of volatile constituents of Haplopappus greenei and studies on the antifungal activity against phytopathogens, J. Agric. Food Chem., 2006, 54, 8, 3146-3150, https://doi.org/10.1021/jf053222v . [all data]

Kürkçüoglu, Hüsnü Can Baser, et al., 2006
Kürkçüoglu, M.; Hüsnü Can Baser, K.; Iscan, G.; Malyer, H.; Kaynak, G., Composition and anticandidal activity of the essential oil of Chaerophyllum byzantinum Boiss., Flavour Fragr. J., 2006, 21, 1, 115-117, https://doi.org/10.1002/ffj.1539 . [all data]

Senatore, Apostolides Arnold, et al., 2006
Senatore, F.; Apostolides Arnold, N.; Piozzi, F.; Formisano, C., Chemical composition of the essential oil of Salvia microstegia Boiss. et Balansa growing wild in Lebanon, J. Chromatogr. A, 2006, 1108, 2, 276-278, https://doi.org/10.1016/j.chroma.2006.01.066 . [all data]

Suleimenov Y.M., Atazhanova G.A., et al., 2006
Suleimenov Y.M.; Atazhanova G.A.; Ozek T.; Demirci B.; Kulyyasov A.T.; Adekenov S.M.; Baser K.H.C., Essential oil composition of three species of Achillea from Kazakhstan, Chem. Nat. Compd. (Engl. Transl.), 2006, 37, 5, 447-450, https://doi.org/10.1023/A:1014471326724 . [all data]

Tabanca, Demirci, et al., 2006
Tabanca, N.; Demirci, B.; Ozek, T.; Kirimer, N.; Can Baser, K.H.; Bedir, E.; Khan, I.A.; Wedge, D.E., Gas chromatographic-mass spectrometric analysis of essential oils from Pimpinella species gathered from Central and Northern Turkey, J. Chromatogr. A, 2006, 1117, 2, 194-205, https://doi.org/10.1016/j.chroma.2006.03.075 . [all data]

Duman, Kartal, et al., 2005
Duman, H.; Kartal, M.; Altun, L.; Demirci, B.; Baser, K.H.C., The essential oil of Stachys laetivirens Kotschy Boiss. ex Rech. fil., endemic in Turkey, Flavour Fragr. J., 2005, 20, 1, 48-50, https://doi.org/10.1002/ffj.1362 . [all data]

Altintas, Kose, et al., 2004
Altintas, A.; Kose, Y.B.; Yucel, E.; Demirci, B.; Baser, K.H.C., Composition of the essential oil of Centaurea dichroa, Chem. Nat. Compd. (Engl. Transl.), 2004, 40, 6, 604-605, https://doi.org/10.1007/s10600-005-0051-9 . [all data]

Baser, Özek, et al., 2004
Baser, K.H.C.; Özek, T.; Kirimer, N.; Deliorman, D.; Ergun, F., Composition of the essential oils of Galium aparine L. and Galium odoratum (L.) Scop. from Turkey, J. Essent. Oil Res., 2004, 16, 4, 305-307, https://doi.org/10.1080/10412905.2004.9698728 . [all data]

Kivcak, Akay, et al., 2004
Kivcak, B.; Akay, S.; Demirci, B.; Baser, K.H.C., Chemical composition of essential oils from leaves and twigs of Pistacia lentiscus, Pistacia lentiscus var. chia, and Pistacia terebinthus from Turkey, Pharm. Biol, 2004, 42, 4-5, 360-366, https://doi.org/10.1080/13880200490519677 . [all data]

Senatore, Apostolides Arnold, et al., 2004
Senatore, F.; Apostolides Arnold, N.; Piozzi, F., Chemical composition of the essential oil of Salvia multicaulis Vahl. var. simplicifolia Boiss. growing wild in Lebanon, J. Chromatogr. A, 2004, 1052, 1-2, 237-240, https://doi.org/10.1016/j.chroma.2004.08.095 . [all data]

Demirci, Baser, et al., 2003
Demirci, B.; Baser, K.H.C.; Yildiz, B.; Bahcecioglu, Z., Composition of the essential oils of six endemic Salvia spp. from Turkey, Flavour Fragr. J., 2003, 18, 2, 116-121, https://doi.org/10.1002/ffj.1173 . [all data]

Demirci and Baser, 2003
Demirci, B.; Baser, K.H.C., Essential oils from the buds of Betula spp. growing in Turkey, Flavour Fragr. J., 2003, 18, 2, 87-90, https://doi.org/10.1002/ffj.1159 . [all data]

Demirci, Dadandi, et al., 2003
Demirci, B.; Dadandi, M.Y.; Paper, D.H.; Franz, G.; Hüsnü Can Baser, K., Chemical Composition of the Essential Oil of Phlomis linearis Boiss. Bal., and Biological Effects on the CAM-Assay: A Safety Evaluation, Z. Naturforsch. C:, 2003, 58, 826-829. [all data]

Demirci, Demirci, et al., 2003
Demirci, B.; Demirci, F.; Baser, K.H.C., Composition of the essential oil of Cotinus coggygria Scop. from Turkey, Flavour Fragr. J., 2003, 18, 1, 43-44, https://doi.org/10.1002/ffj.1149 . [all data]

Erdemoglu, Sener, et al., 2003
Erdemoglu, N.; Sener, B.; Demirci, B.; Baser, K.H.C., The glycosidically bound volatile compounds of Taxus baccata, Chem. Nat. Compd. (Engl. Transl.), 2003, 39, 2, 195-198, https://doi.org/10.1023/A:1024870031960 . [all data]

Hüsnü Can Baser, Demirci, et al., 2002
Hüsnü Can Baser, K.; Demirci, B.; Femirci, F.; Kocak, S.; Akinci, C.; Malyer, H.; Güleryüz, G., Composition and antimicrobial activity of the essential oil of Achellea multifida, Planta Medica, 2002, 68, 10, 941-943, https://doi.org/10.1055/s-2002-34923 . [all data]

Baser, Demirci, et al., 2001
Baser, K.H.C.; Demirci, B.; Tabanca, N.; Özek, T.; Gören, N., Composition of the essential oils of Tanacetum armenum (DC.) Schultz Bip., T. balsamita L., T. chiliophyllum (Fisch. Mey.) Schultz Bip. var. chiliophyllum and T. haradjani (Rech. fil.) Grierson and the enantiomeric distribution of camphor and carvone, Flavour Fragr. J., 2001, 16, 3, 195-200, https://doi.org/10.1002/ffj.977 . [all data]

Kaya, Demirci, et al., 2001
Kaya, A.; Demirci, B.; Baser, K.H.C., The composition of the essential oil of Stachys iberica subsp. stenostachya growing in Turkey, Chem. Nat. Compd. (Engl. Transl.), 2001, 37, 4, 326-328, https://doi.org/10.1023/A:1013762200024 . [all data]

Kirimer N., Tabanea N., et al., 2001
Kirimer N.; Tabanea N.; Demirci B.; Baser K.H.C.; Duman H.; Aytac Z., The essential oil of a new Sideritis species: Sideritis ozturkii Aytac and Aksoy, Chem. Nat. Compd. (Engl. Transl.), 2001, 37, 3, 234-237, https://doi.org/10.1023/A:1012561806033 . [all data]

Özcan, Akgül, et al., 2001
Özcan, M.; Akgül, A.; Bascr, K.H.C.; Özck, T.; Tabanca, N., Essential oil composition of sea fennel (Crithmum maritimum) form Turkey, Nahrung/Food, 2001, 45, 5, 353-356, https://doi.org/10.1002/1521-3803(20011001)45:5<353::AID-FOOD353>3.0.CO;2-4 . [all data]

Tabanca, Kirimer, et al., 2001
Tabanca, N.; Kirimer, N.; Demirci, B.; Demirci, F.; Can Baser, K.H., Composition and antimicrobial activity of the essential oils of Micromeria cristata subsp. phrygia and the enantiomeric distribution of borneol, J. Agric. Food Chem., 2001, 49, 9, 4300-4303, https://doi.org/10.1021/jf0105034 . [all data]

Kirimer, Tabanca, et al., 2000
Kirimer, N.; Tabanca, N.; Özek, T.; Tümen, G.; Baser, K.H.C., Essential oils of annual Sideritis species growing in Turkey, Pharm. Biol., 2000, 38, 2, 106-111, https://doi.org/10.1076/1388-0209(200004)3821-1FT106 . [all data]

Kirimer, Tabanca, et al., 1999
Kirimer, N.; Tabanca, N.; Ozek, T.; Basher, K.H.C.; Tumen, G., Composition of essential oils from two endemic Sideritis species of Turkey, Chem. Natural Comp., 1999, 35, 1, 61-64, https://doi.org/10.1007/BF02238211 . [all data]

Baser, Kürkcüoglu, et al., 1998
Baser, K.H.C.; Kürkcüoglu, M.; Aytac, Z., Composition of the essential oil of Salvia euphratica Montbret ex Bentham var. euphratica from Turkey, Flavour Fragr. J., 1998, 13, 1, 63-64, https://doi.org/10.1002/(SICI)1099-1026(199801/02)13:1<63::AID-FFJ694>3.0.CO;2-Z . [all data]

Notes

Go To: Top, Normal alkane RI, polar column, custom temperature program, References

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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