Fragrant Sesquiterpene Ketones as Trace Constituents in Frankincense Volatile Oil of <i>Boswellia sacra</i>

Niebler, Johannes; Zhuravlova, Katharina; Minceva, Mirjana; Buettner, Andrea

doi:10.1021/acs.jnatprod.5b00836

Cited by 32 publications

(37 citation statements)

References 19 publications

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“…[2] Very recently,t he same authors eventually elucidated the structures of the two odorants possessing the highest FD factor in these analyses as rotundone (15)a nd mustakone (16). [18] Both of these ketones are highly potent trace odorants,and their characterization required the use of an elegant combination of fractionation techniques.I nt his work, the odor of 16 was described as "spicy,woody,slightly fatty,meatbroth-like,a nd balsamic" while 15,awell-known spicya nd peppery odorant, [19] was reported to display "woody,c oniferous,i ncense like" odor close to its detection threshold.…”

Section: Angewandte Chemiementioning

confidence: 99%

The (+)‐cis‐ and (+)‐trans‐Olibanic Acids: Key Odorants of Frankincense

et al. 2016

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Frankincense (olibanum) is one of the oldest aromatic materials used by humans, but the key molecular constituents contributing to its characteristic odor remained unknown. Reported herein is the discovery that (1S,2S)-(+)-trans- and (1S,2R)-(+)-cis-2-octylcyclopropyl-1-carboxylic acids are highly potent and substantive odorants occurring in ppm amounts in all of the frankincense samples analyzed, even those showing radically different volatile compositions. These cyclopropyl-derived acids provide the very characteristic old churchlike endnote of the frankincense odor.

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Section: Angewandte Chemiementioning

confidence: 99%

The (+)‐cis‐ and (+)‐trans‐Olibanic Acids: Key Odorants of Frankincense

et al. 2016

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“…Besides these thermally generated flavors, other ketones like 2,3-butanedione and 3-penten-2-one also increased by 10-and 17-fold, respectively. These ketones possess relatively low aroma thresholds (Niebler, Zhuralova, Minceva, & Buettner, 2016); therefore, their contributions and impacts to the overall flavor profile of roasted pecan may be substantial.…”

Section: Food Chemistrymentioning

confidence: 99%

Characterization of the Volatile Compounds in Raw and Roasted Georgia Pecans by HS‐SPME‐GC‐MS

Gong

Kerrihard

Pegg

2018

Journal of Food Science

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Volatile compounds are responsible for the characteristic aroma of raw and roasted pecans. Yet, much is unknown about the specific effects of roasting on pecan volatiles. In this study, the volatiles of raw “Desirable” pecans from Georgia and 3 roasted pecan samples (175 °C for 5, 10, and 15 min) were determined by HS‐SPME coupled to GC‐MS using stable deuterium‐labeled volatiles as internal standards for quantitation. As expected, roasting markedly impacted the volatile profile of pecans: a total of 63 flavor‐active compounds were identified in roasted samples, including 9 compounds not detected in raw “Desirable” pecans. Pyrazines, notable indicators of the Maillard reaction, were found only in roasted samples and demonstrated continual increases throughout observed roasting times. Furthermore, it was noted that hydrocarbon derivatives showed substantial increases with roasting, likely a result of the degradation of nonvolatile lipids. The observed changes correspond well to prior sensory investigations concerning the impact of roasting on pecan flavor, and explain increases in intensity for roasted, nutty, buttery, and sweet sensory traits. Practical Application The results of this study document the volatile constituents generated during the roasting of pecans, and this may help formulators, who are trying to develop natural and artificial pecan flavors in new food products.

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“…Besides, according to Ohloff et al., 9 and 14 are odorless . Very recently, the same authors eventually elucidated the structures of the two odorants possessing the highest FD factor in these analyses as rotundone ( 15 ) and mustakone ( 16 ) . Both of these ketones are highly potent trace odorants, and their characterization required the use of an elegant combination of fractionation techniques.…”

Section: Figurementioning

confidence: 99%

The (+)‐cis‐ and (+)‐trans‐Olibanic Acids: Key Odorants of Frankincense

et al. 2016

View full text Add to dashboard Cite

Frankincense (olibanum) is one of the oldest aromatic materials used by humans,b ut the key molecular constituents contributing to its characteristic odor remained unknown. Reported herein is the discovery that (1S,2S)-(+ +)-trans-and (1S,2R)-(+ +)-cis-2-octylcyclopropyl-1-carboxylic acids are highly potent and substantive odorants occurring in ppm amounts in all of the frankincense samples analyzed, even those showing radically different volatile compositions. These cyclopropyl-derived acids provide the very characteristic old churchlike endnote of the frankincense odor.

show abstract

Fragrant Sesquiterpene Ketones as Trace Constituents in Frankincense Volatile Oil of Boswellia sacra

Cited by 32 publications

References 19 publications

The (+)‐cis‐ and (+)‐trans‐Olibanic Acids: Key Odorants of Frankincense

The (+)‐cis‐ and (+)‐trans‐Olibanic Acids: Key Odorants of Frankincense

Characterization of the Volatile Compounds in Raw and Roasted Georgia Pecans by HS‐SPME‐GC‐MS

The (+)‐cis‐ and (+)‐trans‐Olibanic Acids: Key Odorants of Frankincense

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