Apiol

• Formula: C₁₂H₁₄O₄
• Molecular weight: 222.2372
• IUPAC Standard InChI: InChI=1S/C12H14O4/c1-4-5-8-6-9(13-2)11-12(10(8)14-3)16-7-15-11/h4,6H,1,5,7H2,2-3H3 Copy

  
• IUPAC Standard InChIKey: QQRSPHJOOXUALR-UHFFFAOYSA-N Copy
• CAS Registry Number: 523-80-8
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: 1,3-Benzodioxole, 4,7-dimethoxy-5-(2-propenyl)-; Benzene, 1-allyl-2,5-dimethoxy-3,4-(methylenedioxy)-; Apiole; Apioline; Parsley apiole; Parsley camphor; 1-Allyl-2,5-dimethoxy-3,4-(methylenedioxy)benzene; 4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole; 1,3-Benzodioxole, 4,7-dimethoxy-5-(2-propen-1-yl)-; NSC 9070; Green Apiol; 5-allyl-4,7-dimethoxy-1,3-benzodioxole; 4,7-Dimethoxy-5-(2-propen-1-yl)-1,3-benzodioxole (apiol)
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
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Phase change data

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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 as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Mass spectrum (electron ionization)

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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

Spectrum

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Additional Data

Gas Chromatography

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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

Kovats' RI, non-polar column, temperature ramp

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

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

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Normal alkane RI, non-polar column, temperature ramp

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

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Normal alkane RI, polar column, temperature ramp

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References

Go To: Top, Phase change data, 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.

Tammann, 1899
Tammann, G., Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1899, 29, 51. [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]

Siani, Ramos, et al., 1999
Siani, A.C.; Ramos, M.F.S.; Menezes-de-Lima, O., Jr.; Ribeiro-dos-Santos, R.; Fernadez-Ferreira, E.; Soares, R.O.A.; Rosas, E.C.; Susunaga, G.S.; Guimarães, A.C.; Zoghbi, M.G.B.; Henriques, M.G.M.O., Evaluation of anti-inflammatory-related activity of essential oils from the leaves and resin of species of Protium, J. Ethnopharmacol., 1999, 66, 1, 57-69, https://doi.org/10.1016/S0378-8741(98)00148-2 . [all data]

da Silva, Zoghbi, et al., 1999
da Silva, M.H.L.; Zoghbi, M.G.B.; Andrade, E.H.A.; Maia, J.G.S., The essential oils of Peperomia pellucida Kunth and P. circinnata link var. circinnata, Flavour Fragr. J., 1999, 14, 5, 312-314, https://doi.org/10.1002/(SICI)1099-1026(199909/10)14:5<312::AID-FFJ835>3.0.CO;2-B . [all data]

Javidnia, Miri, et al., 2005
Javidnia, K.; Miri, R.; Kamalinejad, M.; Edraki, N., Chemical composition of Ferula persica Wild. essential oil from Iran, Flavour Fragr. J., 2005, 20, 6, 605-606, https://doi.org/10.1002/ffj.1496 . [all data]

Afsharypuor and Suleimany, 2002
Afsharypuor, S.; Suleimany, M., Volatile oil constituents of Brassica oleracea var. gongylodes seeds, J. Essent. Oil Res., 2002, 14, 1, 18-19, https://doi.org/10.1080/10412905.2002.9699748 . [all data]

Pérez, Navarro, et al., 2007
Pérez, R.A.; Navarro, T.; de Lorenzo, C., HS-SPME analysis of the volatile compounds from spices as a source of flavour in 'Campo Real' table olive preparations, Flavour Fragr. J., 2007, 22, 4, 265-273, https://doi.org/10.1002/ffj.1791 . [all data]

Rahimi-Nasrabadi, Gholivand, et al., 2009
Rahimi-Nasrabadi, M.; Gholivand, M.B.; Batooli, H.; Vatanara, A., Chemical composition of the essential oil from leaves and flowering aerial parts of Psammogeton canscens (DC). Vake from Iran, J. Medicinal Plants, 2009, 8, 31, 82-86. [all data]

Bousaada, Ammar, et al., 2008
Bousaada, O.; Ammar, S.; Saidana, D.; Chriaa, J.; Chraif, I.; Daami, M.; Helal, A.N.; Mighri, Z., Chemical composition and antimicrobial activity of volatile components from capitula and aerial parts of Rhaponticum acaule DC growing wild in Tunisia, Microbiol. Res., 2008, 163, 1, 87-95, https://doi.org/10.1016/j.micres.2007.02.010 . [all data]

Yassa and Akhani, 2008
Yassa, N.; Akhani, H., The essential oils composition in two species of the genus Eriocycla Lindl. (Apiaceae) from Iran, 2008, retrieved from http://biology.ut.ac.ir/members/akhani/PdfReprintNumber/27.pdf. [all data]

Yassa and Akhani, 2007
Yassa, N.; Akhani, H., The essential oils composition in two species of the genus Eriocycla Lindl. (Apiaceae) from Iran, 2007, retrieved from http://biology.ut.ac.ir/members/akhani/PdfReprintNumber/27.pdf. [all data]

Bozin, Mimicá-Dukic, et al., 2006
Bozin, B.; Mimicá-Dukic, N.; Simin, N.; Anackov, G., Characterization of the volatile composition of essential oils of some lamiaceae spices and the antimicrobial and antioxidant activities of the entire oils, J. Agric. Food Chem., 2006, 54, 5, 1822-1828, https://doi.org/10.1021/jf051922u . [all data]

Kurowska and Galazka, 2006
Kurowska, A.; Galazka, I., Essential oil composition of the parsley seed of cultivars marketed in Poland, Flavour Fragr. J., 2006, 21, 1, 143-147, https://doi.org/10.1002/ffj.1548 . [all data]

Melkani, Dev, et al., 2005
Melkani, A.B.; Dev, V.; Beauchamp, P.S.; Negi, A.; Mehta, S.P.S.; Melkani, K.B., Constituents of the essential oil of a new chemotype of Elsholtzia strobilifera Benth., Biochem. Syst. Ecol., 2005, 33, 4, 419-425, https://doi.org/10.1016/j.bse.2004.10.009 . [all data]

Couladis, Özcan, et al., 2003
Couladis, M.; Özcan, M.; Tzakou, O.; Akgül, A., Comparative essential oil composition of various parts of the turpentine tree (Pistacia terebinthus L) growing wild in Turkey, J. Sci. Food Agric., 2003, 83, 2, 136-138, https://doi.org/10.1002/jsfa.1295 . [all data]

Orav, Kailas, et al., 2003
Orav, A.; Kailas, T.; Jegorova, A., Composition of the essential oil of dill, celery, and parsley from Estonia, Proc. Est. Acad. Sci. Chem., 2003, 52, 4, 147-154. [all data]

Velasco-Negueruela, Pérez-Alonso, et al., 2003
Velasco-Negueruela, A.; Pérez-Alonso, M.J.; Pérez de Paz, P.L.; Palá-Paúl, J.; Sanz, J., Analysis by gas chromatography-mass spectrometry of the essential oils from the aerial parts of Rutheopsis herbanica (Bolle) Hans. Kunk., gathered in Fuerteventura (Canary Islands), J. Chromatogr. A, 2003, 984, 1, 159-162, https://doi.org/10.1016/S0021-9673(02)01742-9 . [all data]

Maia, Zohhbi, et al., 1998
Maia, J.G.S.; Zohhbi, M.G.B.; Andrade, E.H.A.; Santos, A.S.; da Silva, M.H.L.; Luz, A.I.R.; Bastos, C.N., Constituents of the essential oil of Piper aduncum L. growing wild in the Amazon region, Flavour Fragr. J., 1998, 13, 4, 269-272, https://doi.org/10.1002/(SICI)1099-1026(1998070)13:4<269::AID-FFJ744>3.0.CO;2-A . [all data]

Marozzi, Gambaro, et al., 1982
Marozzi, E.; Gambaro, V.; Saligari, E.; Mariani, R.; Lodi, F., Use of the retention index in gas chromatographic studies of drugs, J. Anal. Toxicol., 1982, 6, 4, 185-192, https://doi.org/10.1093/jat/6.4.185 . [all data]

Chu, Liu, et al., 2011
Chu, S.S.; Liu, S.L.; Liu, Q.Z.; Liu, Z.L.; Du, S.S., Composition and toxicity of Chinese Dracocephalum moldavica (Labiatae) essential oil against two grain storage insects, J. Med. Plants Res., 2011, 5, 21, 5262-5267. [all data]

Wang, Xu, et al., 2011
Wang, J.; Xu, L.; Yang, L.; Liu, Z.; Zhou, L., Composition, antibacterial and antioxidant activities of essential oils from Ligusticum sinense and L. jaholense (Unvelliferae) from China, Rec. Nat. Prod., 2011, 5, 4, 314-318. [all data]

Xu, Tang, et al., 2010
Xu, X.; Tang, Z.; Liang, Y., Comparative analysis of plant essential oils by GC-MS coupled with integrated chemometric resolution methods, Anal. Methods, 2010, 2, 4, 359-367, https://doi.org/10.1039/b9ay00213h . [all data]

Singh, Marimuthu, et al., 2006
Singh, G.; Marimuthu, P.; de Heluani, C.S.; Catalan, C.A.N., Antioxidant and biocidal activities of Carum nigrum (seed) essential oil, oleoresin, and their selected components, J. Agric. Food Chem., 2006, 54, 1, 174-181, https://doi.org/10.1021/jf0518610 . [all data]

Couladis, Özcan, et al., 2004
Couladis, M.; Özcan, M.; Tzakou, O.; Akgül, A., Menengic (Pistacia terebinthus L.) agacinin degisik organlarinda ucucu yag bilesimi, Bitkisel Ilac Hammaddeleri Toplantisi, Bildiriler, 29-31 Mayis 2002, 2004, 6. [all data]

Lo Cantore, Iacobellis, et al., 2004
Lo Cantore, P.; Iacobellis, N.S.; de Marco, A.; Capasso, F.; Senatore, F., Antibacterial activity of Coriandrum sativum L. and Foeniculum vulgare Miller Var. vulgare (Miller) essential oils, J. Agric. Food Chem., 2004, 52, 26, 7862-7866, https://doi.org/10.1021/jf0493122 . [all data]

Andrade, Maia, et al., 2000
Andrade, E.H.A.; Maia, J.G.S.; Zoghbi, M.G.B., Aroma volatile constituents of Brazilian varieties of mango fruit, J. Food Comp. Anal., 2000, 13, 1, 27-33, https://doi.org/10.1006/jfca.1999.0841 . [all data]

Wei A. and Shibamoto T., 2007
Wei A.; Shibamoto T., Antioxidant activities and volatile constituents of various essential oils, J. Agric. Food Chem., 2007, 55, 5, 1737-1742, https://doi.org/10.1021/jf062959x . [all data]

Notes

Go To: Top, Phase change data, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  Tfus	Fusion (melting) point
  ΔvapH	Enthalpy of vaporization

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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