β-Asarone

Formula: C₁₂H₁₆O₃
Molecular weight: 208.2536
IUPAC Standard InChI: InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5-
IUPAC Standard InChIKey: RKFAZBXYICVSKP-WAYWQWQTSA-N
CAS Registry Number: 5273-86-9
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:
- Asarone
- (E)-Azarone
Other names: Benzene, 1,2,4-trimethoxy-5-(1-propenyl)-, (Z)-; cis-Asarone; cis-β-Asarone; (Z)-Asarone; Benzene, 1,2,4-trimethoxy-5-propenyl-, (Z)-; cis-Isoasarone; cis-Isoelemicin; (Z)-5-Propenyl-1,2,4-trimethoxybenzene; (Z)-β-Asarone; (Z)-Isoelemicin; 1,2,4-Trimethoxy-5-[(1Z)-1-propenyl]benzene; (Z)-1,2,4-Trimethoxy-5-(prop-1-en-1-yl)benzene; (Z)-Azarone; 2,4,5-trimethoxypropen-1-ylbenzene
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Other data available:
- Mass spectrum (electron ionization)
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Gas Chromatography

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

Kovats' RI, non-polar column, temperature ramp

Column type	Active phase	I	Reference	Comment
Capillary	BP-1	1599.	Raina, Srivastava, et al., 2003	25. m/0.32 mm/0.25 μm, N2, 5. K/min, 220. C @ 15. min; T_start: 60. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	HP-101	1561.	Politeo, Jukic, et al., 2007	25. m/0.20 mm/0.20 μm, Helium, 70. C @ 2. min, 3. K/min, 200. C @ 15. min
Capillary	HP-5	1631.	Xian Q., Chen H., et al., 2006	30. m/0.25 mm/0.25 μm, He, 3. K/min, 220. C @ 20. min; T_start: 50. C
Capillary	DB-5	1629.	Zhang, Xu, et al., 2005	30. m/0.25 mm/0.25 μm, N2, 45. C @ 10. min, 2.5 K/min, 180. C @ 20. min
Capillary	HP-5	1621.	Oprean, Tamas, et al., 1998	He, 3. K/min; Column diameter: 0.26 mm; Phase thickness: 0.25 μm; T_start: 60. C; T_end: 240. C
Capillary	DB-1	1640.	Stashenko, Prada, et al., 1996	60. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 3.5 K/min; T_end: 250. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	1641.1	Andriamaharavo, 2014	30. m/0.25 mm/0.25 μm, He; Program: 60C (1 min) => 5 C/min => 210C => 10 C/min => 280C (15 min)

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-5MS	1583.	Marongiu, Piras, et al., 2005	30. m/0.25 mm/0.25 μm, He, 60. C @ 30. min, 3. K/min; T_end: 280. C
Capillary	HP-5	1626.	Yassa, Akhani, et al., 2003	30. m/0.25 mm/0.32 μm, He, 60. C @ 30. min, 5. K/min; T_end: 250. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	CP Sil 8 CB	1617.	Radusiene, Judzentiene, et al., 2007	50. m/0.32 mm/0.25 μm, Helium; Program: 60 0C (2 min) 5 0C/min -> 160 0C (1 min) 10 0C/min -> 280 0C (3 min)
Capillary	HP-5 MS	1631.	Xian, Chen, et al., 2006	30. m/0.25 mm/0.25 μm, Helium; Program: 40 0C (3 min) 6 0C/min -> 150 0C (1 min) 10 0C/min -> 250 0C (10 min)
Capillary	HP-5MS	1596.	Deng, Li, et al., 2004	30. m/0.25 mm/0.25 μm, He; Program: 60C => 10C/min => 160C => 12C/min => 300C (5min)
Capillary	Methyl Silicone	1579.	Grundschober, 1991	Program: not specified

Normal alkane RI, polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	2252.	Gyawali and Kim, 2009	60. m/0.25 mm/0.25 μm, Helium; Program: 40 0C (3 min) 2 0C/min -> 150 0C 4 0C/min -> 220 0C (20 min)
Capillary	Carbowax 20M	2215.	Vinogradov, 2004	Program: not specified

References

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Raina, Srivastava, et al., 2003
Raina, V.K.; Srivastava, S.K.; Syamasunder, K.V., Essential oil composition of Acorus calamus L. from the lower region of the Himalayas, Flavour Fragr. J., 2003, 18, 1, 18-20, https://doi.org/10.1002/ffj.1136 . [all data]

Politeo, Jukic, et al., 2007
Politeo, O.; Jukic, M.; Milos, M., Chemical Composition and Antioxidant Activity of Free Volatile Aglycones from Laurel (Laurus nobilis L.) Compared to Its Essential Oil, Croatica Chem. Acta, 2007, 80, 1, 121-126. [all data]

Xian Q., Chen H., et al., 2006
Xian Q.; Chen H.; Zou H.; Yin D., Chemical composition of essential oils of two submerged macrophytes, Ceratophyllum demersum L. and Vallisneria spiralis L., Flavour Fragr. J., 2006, 21, 3, 524-526, https://doi.org/10.1002/ffj.1588 . [all data]

Zhang, Xu, et al., 2005
Zhang, F.; Xu, Q.; Fu, S.; Ma, X.; Xiao, H.; Liang, X., Chemical constituents of the essential oil of Asarum forbesii Maxim (Aristolochiaceae), Flavour Fragr. J., 2005, 20, 3, 318-320, https://doi.org/10.1002/ffj.1423 . [all data]

Oprean, Tamas, et al., 1998
Oprean, R.; Tamas, M.; Sandulescu, R.; Roman, L., Essential oils analysis. I. Evaluation of essential oils composition using both GC and MS fingerprints, J. Pharm. Biomed. Anal., 1998, 18, 4-5, 651-657, https://doi.org/10.1016/S0731-7085(98)00283-0 . [all data]

Stashenko, Prada, et al., 1996
Stashenko, E.E.; Prada, N.Q.; Martínez, J.R., HRGC/FID/NP and HRGC/MSD study of Colombian Ylang-Ylang (Cananga odorata) oils obtained by different extraction techniques, J. Hi. Res. Chromatogr., 1996, 19, 6, 353-358, https://doi.org/10.1002/jhrc.1240190609 . [all data]

Andriamaharavo, 2014
Andriamaharavo, N.R., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2014. [all data]

Marongiu, Piras, et al., 2005
Marongiu, B.; Piras, A.; Porcedda, S.; Scorciapino, A., Chemical composition of the essential oil and supercritical CO₂ extract of Commiphora myrrha (Nees) Engl. and of Acorus calamus L., J. Agric. Food Chem., 2005, 53, 20, 7939-7943, https://doi.org/10.1021/jf051100x . [all data]

Yassa, Akhani, et al., 2003
Yassa, N.; Akhani, H.; Aqaahmadi, M.; Salimian, M., Essential oils from two endemic species of Apiaceae from Iran, Z. Naturforsch. C:, 2003, 58, 459-463. [all data]

Radusiene, Judzentiene, et al., 2007
Radusiene, J.; Judzentiene, A.; Peciulyte, D.; Janulis, V., Essential Oil Composition and Antimicrobial Assay of Acorus calamus Leaves from Different Wild Populations, Plant Genetic Resources: Characterization and Utilization, 2007, 5, 1, 37-44, https://doi.org/10.1017/S1479262107390928 . [all data]

Xian, Chen, et al., 2006
Xian, Q.-M.; Chen, H.-D.; Zou, H.-H., Allelopathic activity of volatile substance from submerged macrophytes on Microcystin aeruginosa, Acta Ecologica Sinica, 2006, 26, 11, 3549-3554, https://doi.org/10.1016/S1872-2032(06)60054-1 . [all data]

Deng, Li, et al., 2004
Deng, C.; Li, N.; Zhang, X., Rapid determination of essential oil in Acorus tatarinowii Schott. by pressurized hot water extraction followed by solid-phase microextraction and gas chromatography-mass spectrometry, J. Chromatogr. A, 2004, 1059, 1-2, 149-155, https://doi.org/10.1016/j.chroma.2004.10.005 . [all data]

Grundschober, 1991
Grundschober, F., The identification of individual components in flavourings and flavoured foods, Z. Lebensm. Unters. Forsch., 1991, 192, 6, 530-534, https://doi.org/10.1007/BF01202508 . [all data]

Gyawali and Kim, 2009
Gyawali, R.; Kim, K.-S., Volatile organic compounds of medicinal values from Nepalese Acorus calamus L., Kathmandu Univ. J. Sci. Eng. Technol., 2009, 5, II, 51-65. [all data]

Vinogradov, 2004
Vinogradov, B.A., Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]

Notes

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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