Proceedings of the IConSSE FSM SWCU (2015), pp. BC.61–63 ISBN: 978-602-1047-21-7
SWUP BC.61
Oxidation against to -guaiene at various time of aeration
Ilmimada Harfiya*, Edi Priyo Utomo, Warsito
aDepartment of Chemistry, Brawijaya University. Jl. Veteran Malang, 65145 Indonesia
Email: *harfiya.ilmimada@yahoo.com
Abstract
Deuterium-labeled guaiane derivatives and the precursors, namely -guaiene, was synthesized in good yields as GCMS internal standards for comparing the behavior of -guaiene autoxidative conditions. It was found that approximately 99% of --guaiene poured into vial bottle and added water then flowed oxygen at ambient temperature was autoxidized after 6 days and up to 35% of rotundone was formed during this period. The results indicate the feasibility of rapid changes of aroma profiles of herbs and other plant materials over time when exposed to air.
Keywords -guaiene, autoxidation, rotundone
1. Introduction
Sesquiterpenes are an important aroma source and have long been used as fragrances in the perfumery and cosmetic industries (Ansari & Curtis,1974).Patchouli oil is an important raw material for the perfume and cosmetics industries, besides being used as a natural
additive for food flavoring. -guaiene is the second main component after patchouli alcohol
in patchouli oil (Sundaresan et al.,2009).
Transformation of -guaiene into fine chemicals by oxidation reaction was also reported by other researcher. It applied various different oxidation times. Oxidation using -guaiene coated onto filter paper and exposed to air at ambient temperature was autoxidized (Huang et al.,2015). This result will be reported oxidation of -guaiene using pure oxidation.
2. Materials and methods
The materials used for research including -guaiene oil 96% from patchuoli oil. Other materials were some chemicals used as bought from the manufacturer or as mentioned, including pure oxygen, ethyl acetate, magnesium sulfate anhydrate (Merck), and aquadest.
0.1 g guaiene oil poured into vial bottle and 10 mL aquadest, and then the mixture was aerated with oxigen at flow rate 90 mL/minute. The aeration was varied at various time. After aeration, the mixture was partitioned with 30 mL ethyl acetate. Organic phase was separated and dried under magnesium sulfate anhydrate. The product was monitored by GCMS-QP2010S, completed with column RTX-MSS, sample was injected at 1 µL, at 250oC for port injector, and 5 mL/min for He gas flowrate.
3. Results and discussion
Oxidation against to α -guaiene at various time of aeration
SWUP BC.62
Figure 1.Chromatogram of standard -guaiene.
Figure 2.Chromatogram of oxidation reaction product of guaiene.
Table 1.Tabulation of standard-guaiene.
Peak
number tR(min) Area (%) Compounds MW (SI)
1 14.956 942578 Trans-caryophyllene 204(88)
2 15.106 122436867 -guaiene 204(95)
Table 2.Tabulation of the oxidation reaction product of-guaiene.
Peak
number tR(min) Area (%) Compounds MW (SI)
1 15.041 7798481 -guaiene 204 (89)
2 15.967 18839469 (-)-Caryophyllene oxide 220 (86)
3 16.679 1872429 Unknown 224 (85)
4 17.308 2153497 patchulane 220 (85)
5 17.746 2934267 Unknown 332 (84)
6 17.992 1690380 Trans-Caryophyllene 218 (86) 7 19.006 1155837 LIMONENEDIOXIDE 1 168 (86)
8 19.348 1908479 Unknown 208 (85)
9 19.581 2593360 Unknown 208 (84)
10 19.755 12889445 3-rotundone 218 (92)
Note:*The compounds was characterized from library of the GC-MS with wiley 7 as reference.
I. Harfiya, E.P. Utomo, Warsito
SWUP BC.63
The product of oxidation againts to -guaiene at 6 days was monitored by GCMS-QP2010S, completed with column RTX-MSS, sample was injected at 1 µL, at 250oC for port injector, and 5 mL/min for He gas flowrate. provided shown on Figure 2. In general, it was found 10 compounds detected, the product of oxidation still detected -guaiene at retention time (tR) 15.041 min. The novel product was found at retention time (tp) 19.755 min with molecular weight 218 and SI 92.
4. Conclusion and remarks
Guaiene oxidation were done by various time. It was found that approximately 96% -guaiene aerated by pure oxigen at air ambient temperature after 124 h and up to 15% of rotundone was formed during this period.
References
Ansari, H., & Curtis, A., (1974) Sesquiterpenes in the perfumery industry.J. Soc. Cosmet. Chem.,25, 203 231.
Huang, A.-C., Sefton, M.A., & Taylor, D.K. (2015). Comparison of the formation of peppery and woody sesquiterpenes derived from -guaiene and -bulnesene under aerial oxidative conditions. Journal of Agricultural and Food Chemistry,63, 1932 1938.
