Characterisation of pyrazines in galbanum oil

Bramwell, A. F.; Burrell, J.W.K.; Riezebos, G.

doi:10.1016/s0040-4039(01)88391-x

Cited by 44 publications

(18 citation statements)

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“…Subsequently this compound was also reported in peas (Murray et al, 1970), in galbanum oil (Bramwell et al, 1969), and in coffee (Friedel et al, 1971). Due to the potency and unusual character of this compound, several reports have been published which describe the synthesis and odor properties of structurally related compounds (Seifert et al, 1970(Seifert et al, , 1972.…”

mentioning

confidence: 76%

Organoleptic properties of some alkyl-substituted alkoxy- and alkylthiopyrazines

Parliment¹,

Epstein²

1973

J. Agric. Food Chem.

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2-Methoxy-3-isobutylpyrazine has previously been reported to be an extremely potent flavoring material with a characteristic aroma of bell peppers. Twenty-one compounds structurally related to this molecule have been synthesized in an attempt to determine structural variations of the molecule which may be made and still retain the intense bell pepper note. For this flavor effect, the alkyl chain can vary from CB to at least CS; the effect is reduced by Cg. Replacing the methoxy group by ethoxy markedly reduces the effect, and it disappears with butoxy substitution. Adding a second alkyl function on the ring reduces the bell pepper character. The effect is not limited to the 2,3 isomer, since the 2,6 isomer possesses a similar note. A most surprising result is the fact that the oxygen of the methoxy group may be replaced by sulfur with little change in character.The compound having the characteristic aroma of bell peppers was identified as 2-methoxy-3-isobutylpyrazine (structure I, R1 = isobutyl) and was shown to possess an extremely low odor threshold (Buttery et al., 1969). Subsequently this compound was also reported in peas (Murray et al., 1970), in galbanum oil (Bramwell et al., 1969), and in coffee (Friedel et al., 1971). Due to the potency and unusual character of this compound, several reports have been published which describe the synthesis and odor properties of structurally related compounds (Seifert et al., 1970(Seifert et al., , 1972. This report extends the previous work for the purpose of further defining the basic chemical structure which is responsible for the intense bell pepper note.There are a number of ways of modifying the basic 2-methoxy-3-isobutylpyrazine molecule. The effect of varying alkyl chain length of R1 in structure I is one obvious choice. Other ways of varying the molecule include: investigating other positional isomers (structures I1 and VI); preparing the dialkyl-substituted methoxy compounds (111); replacing the methoxy by higher alkoxy (IV); and replacing the oxygen by sulfur (V and VI).Gas-Liquid Chromatography. Since the synthetic procedures described below result in a mixture of the 2,3-General Foods' Technical Center, White Plains, New York 10625. and 2,6-chloroalkylpyrazine isomers (Lutz et al., 1964), final purification of the desired isomer was achieved by gas-liquid chromatography. The samples were purified on a Ys in. X 6 ft column packed with 10% DEGS on 60/80 mesh Anakrom ABS in a Perkin-Elmer Model 900 gas chromatograph. Helium carrier gas flow was 30 ml/min and detection was by flame ionization. Temperature programming was utilized and the purified compound was trapped by condensation in a Dry Ice-cooled melting point capillary tube.General Synthetic Procedure. 2-C hloro-3-methylpyrazine containing a small amount of 2-chloro-6-methylpyrazine was prepared as described in the literature (Hirschberg and Spoerri, 1961;Lutz et al., 1964). This mixture was converted to the corresponding alkoxymethylpyrazine or thioalkoxy-methylpyrazine by reaction with the appropriate ...

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confidence: 76%

Organoleptic properties of some alkyl-substituted alkoxy- and alkylthiopyrazines

Parliment¹,

Epstein²

1973

J. Agric. Food Chem.

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“…However, several investigative groups have reported that galbanum oil also contains numerous pyrazine compounds and these are listed in Table 7. TABLE 6 Pyrazines Reported in Dairy Products pyrazine methylpyrazine 2,3-dimethylpyrazine 2,5-dimethylpyrazine 2,6-dimethylpyrazine trimethylpyrazine tetramethylpyrazine 2-ethyl-S-methylpyrazine 2-ethyl-6-methylpyrazine 2-vinyl-5-methylpyrazine 2-vinyl-6-methylpyrazine TABLE 7 Pyrazines Reported in Galbanum Oil tetramethylpyrazine 2,6-diethyl-3-methylpyrazine 2,3-dimethyl-5-ethylpyrazine 2-butyl-3-methoxypyrazine 2-isobutyl-3-methoxypyTazine 2-isopropyl-3-methoxypyrazine 2-methoxy-3-isopropyl-S-methylpyrazine 2,6-dimethoxy-3-isopropyl-5-methylpyrazine For example, Bramwell et al (1969) identified 2-methoxy-3-sec-butylpyrazine at a concentration estimated to be less than 0.05% of the total volatiles present. They also reported that other pyrazines were present and tentatively identified 2-isobutyl-3-me thoxy pyrazine.…”

Section: Galbanum Oilmentioning

confidence: 99%

“…Katoetal., 1972Flanagan et al, 19721971a,b;Wobbenetal., 1971Bramwell et al, 1969 von Sydow and Anjou, 1969 Wilkens and Lin, 1970Kosugeet al, 1962Bondarovich et al, 1967Friedel et al, 1971Vianiet al, 1965 Stoffelsma et al, Deck and Chang, 1965Walradt et al, 1970Kinlin etal., 1970Wang and Odell, 1972Sheldon etal., 1972Watanabe and Sato, 1971 Leibich etal., 1972 P. Wang etal., 1972, 1969Reineccius et al, 1972Flament et al, 1967van Praag et al, 1968Marion et al, 1967Deck etal., 1973Rizzi, 1967Collins, 1971Manley and Fagerson, 1970Koehler etal., 1969vanderWal, 1971S. Katoetal., 1970 Sapers etal., 1971 Koehler and Odell, 1970Koehler etal., 1971Rizzi, 1972Davison and Wiggins, 1956 Dawes and Edwards, 1966Shigematsu et al, 1972Fujimaki et al, 1972Burrell etal., 1970 GLC X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X MS X X X X X X X X X X X X X X X X X X X X X .…”

Section: Table44mentioning

confidence: 99%

Pyrazines in foods

Maga

Sizer

Myhre

1973

C R C Critical Reviews in Food Technology

113

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“…3‐Isobutyl‐2‐methoxypyrazine was first identified in green capsicum (bell pepper), where it was found to be the principal compound responsible for the distinct capsicum odour (Buttery et al ., ). Subsequently, the compound 3‐ sec ‐butyl‐2‐methoxypyrazine (SBMP) was identified from galbanum oil (Bramwell et al ., ), where it is the major odorant, and IPMP was identified in green peas (Murray et al ., ). 3‐Isopropyl‐2‐methoxypyrazine is commonly described as ‘sweet pea‐like’ and ‘asparagus‐like’ (Murray et al ., ), but it is also sometimes associated with the earthy aroma reminiscent of roots (Gerber, ).…”

Section: Introductionmentioning

confidence: 99%

A methyltransferase essential for the methoxypyrazine‐derived flavour of wine

et al. 2013

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SUMMARYMethoxypyrazines are a family of potent volatile compounds of diverse biological significance. They are used by insects and plants in chemical defence, are present in many vegetables and fruit and, in particular, impart herbaceous/green/vegetal sensory attributes to wines of certain varieties, including Cabernet Sauvignon. While pathways for methoxypyrazine biosynthesis have been postulated, none of the steps have been confirmed genetically. We have used the F 2 progeny of a cross between a rapid flowering grapevine dwarf mutant, which does not produce 3-isobutyl-2-methoxypyrazine (IBMP), and Cabernet Sauvignon to identify the major locus responsible for accumulation of IBMP in unripe grape berries. Two candidate methyltransferase genes within the locus were identified and one was significantly associated with berry IBMP levels using association mapping. The enzyme encoded by this gene (VvOMT3) has high affinity for hydroxypyrazine precursors of methoxypyrazines. The gene is not expressed in the fruit of Pinot varieties, which lack IBMP, but is expressed in Cabernet Sauvignon at the time of accumulation of IBMP in the fruit. The results suggest that VvOMT3 is responsible for the final step in methoxypyrazine synthesis in grape berries and is the major determinant of IBMP production.

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Characterisation of pyrazines in galbanum oil

Cited by 44 publications

References 4 publications

Organoleptic properties of some alkyl-substituted alkoxy- and alkylthiopyrazines

Organoleptic properties of some alkyl-substituted alkoxy- and alkylthiopyrazines

Pyrazines in foods

A methyltransferase essential for the methoxypyrazine‐derived flavour of wine

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