(5R,6R)-3,6-Dimethyl-5-(prop-1-en-2-yl)-6-vinyl-6,7-dihydrobenzofuran-4(5H)-one

Formula: C₁₅H₁₈O₂
Molecular weight: 230.3022
IUPAC Standard InChI: InChI=1S/C15H18O2/c1-6-15(5)7-11-12(10(4)8-17-11)14(16)13(15)9(2)3/h6,8,13H,1-2,7H2,3-5H3/t13-,15-/m1/s1
IUPAC Standard InChIKey: ZVMJXSJCBLRAPD-UKRRQHHQSA-N
CAS Registry Number: 20493-56-5
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Stereoisomers:
- Epicurzerenone
Other names: 4(5H)-Benzofuranone, 6-ethenyl-6,7-dihydro-3,6-dimethyl-5-(1-methylethenyl)-, (5R,6R)-; 4(5H)-Benzofuranone, 6,7-dihydro-5?-isopropenyl-3,6?-dimethyl-6-vinyl-; 4(5H)-Benzofuranone, 6-ethenyl-6,7-dihydro-3,6-dimethyl-5-(1-methylethenyl)-, trans-; 4(5H)-Benzofuranone, 6-ethenyl-6,7-dihydro-3,6-dimethyl-5-(1-methylethenyl)-; Curzerenone
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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	1574.	Srivastava, Srivastava, et al., 2006	30. m/0.32 mm/0.25 μm, N2, 5. K/min, 220. C @ 3. min; T_start: 60. C
Capillary	BP-1	1576.	Raina, Srivastava, et al., 2002	25. m/0.55 mm/0.25 μm, N2, 5. K/min, 220. C @ 15. min; T_start: 60. C
Capillary	Methyl Silicone	1595.5	Rao, Rajanikanth, et al., 1989	4. K/min, 250. C @ 15. min; Column length: 12. m; Column diameter: 0.5 mm; T_start: 70. 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	1609.6	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	Polydimethyl siloxane with 5 % Ph	1590.	Priya, Prathapan, et al., 2012	Helium, 5. K/min, 200. C @ 25. min; Column length: 30. m; T_start: 80. C
Capillary	DB-1	1610.	Facundo, Pinto, et al., 2005	30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 5. K/min, 250. C @ 15. min
Capillary	DB-5MS	1568.	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

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

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Column type	Active phase	I	Reference	Comment
Capillary	CP Sil 5 CB	1599.	Phan, Van, et al., 1998	N2; Column length: 25. m; Program: not specified

Normal alkane RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	CP-Wax 52CB	2278.	Mau, Lai, et al., 2003	60. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 40. C; T_end: 220. C

Normal alkane RI, polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	2240.	Phan, Van, et al., 1998	Program: not specified

References

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Srivastava, Srivastava, et al., 2006
Srivastava, A.K.; Srivastava, S.K.; Syamsundar, K.V., Volatile composition of Curcuma angustifolia Roxb. rhizome from central and southern India, Flavour Fragr. J., 2006, 21, 3, 423-426, https://doi.org/10.1002/ffj.1680 . [all data]

Raina, Srivastava, et al., 2002
Raina, V.K.; Srivastava, S.K.; Jain, N.; Ahmad, A.; Syamasundar, K.V.; Aggarwal, K.K., Essential oil composition of Curcuma longa L. cv. Roma from the plains of northern India, Flavour Fragr. J., 2002, 17, 2, 99-102, https://doi.org/10.1002/ffj.1053 . [all data]

Rao, Rajanikanth, et al., 1989
Rao, A.S.; Rajanikanth, B.; Seshadri, R., Volatile aroma components of Curcuma amada Roxb., J. Agric. Food Chem., 1989, 37, 3, 740-743, https://doi.org/10.1021/jf00087a036 . [all data]

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

Priya, Prathapan, et al., 2012
Priya, R.; Prathapan, A.; Raghu, K.G.; Menon, A.N., Chemical composition and in vitro antioxidative potential of essential oil isolated from Curcuma longa L. leaves, Asian Pacific Journal of Tropical Biomedicine, 2012, 2, 2, s695-s699, https://doi.org/10.1016/S2221-1691(12)60298-6 . [all data]

Facundo, Pinto, et al., 2005
Facundo, V.A.; Pinto, A.C.; Rezende, C.M., Aroma compounds and volatile chemical composition of Ruellia menthoides (Nees) Hiern, Flavour Fragr. J., 2005, 20, 1, 93-95, https://doi.org/10.1002/ffj.1380 . [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]

Phan, Van, et al., 1998
Phan, M.G.; Van, N.H.; Phan, T.S., Sesquiterpenoids fron the rhizomes of Curcuma aff. aeruginosa Roxb. of Vietnam, Tap chi Hoa hoc, 1998, 36, 3, 67-72. [all data]

Mau, Lai, et al., 2003
Mau, J.-L.; Lai, E.Y.C.; Wang, N.-P.; Chen, C.-C.; Chang, C.-H.; Chyau, C.-C., Composition and antioxidant activity of the essential oil from Curcuma zedoaria, Food Chem., 2003, 82, 4, 583-591, https://doi.org/10.1016/S0308-8146(03)00014-1 . [all data]

Notes

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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