G. Ohloff’s research while affiliated with Max-Planck-Institut für Kohlenforschung and other places

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Publications (207)


Pyrazines III Condensation Des Dihydropyrazines Avec Les Composés Carbonyles: Synthèse De Pyrazines Substituées Et De Dihydro‐6, 7‐5E‐Cyclopenta [b] pyrazines
  • Article

September 2010

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18 Reads

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2 Citations

Bulletin des Sociétés Chimiques Belges

Ivon Flament

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Philippe Sonnay

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Günther Ohloff

Dihydropyrazines have been found to condense easily and in good yields with carbonyl compounds. 2,3-Dihydropyrazines were treated with aliphatic, terpenic, aromatic and furan aldehydes and with aliphatic and alicyclic ketones leading to trisubstituted pyrazines. When α, β-unsaturated carbonyl compounds are used the formation of 6,7-dihydro-5E-cyclopenta [b] pyrazines is observed. When autocondensation of α-aminoacetone is conducted in the presence of aldehydes these compounds react immediately with the intermediate 3,6-dihydropyrazine to give trisubstituted pyrazines.



Über Verbindungen der γ‐Jonon‐Reihe

January 2006

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11 Reads

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3 Citations

Es wird die Synthese von cis-3-Acetoxy-Verbindungen der Jonon-Reihe beschrieben. Ihre Pyrolyse führt zu γ-Jonon und Dihydro-γ-jonon.


Zur photosensibilisierten O2‐Übertragung auf (+)‐Caren‐(3)

January 2006

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12 Reads

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10 Citations

Klaus Gollnick

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Siegfried Schroeter

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Günther Ohloff

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[...]

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GüNther O. Schenck

Die photosensibilisierte O2-Übertragung auf (+)-Caren-(3) (1) führt, nach Reduktion der dabei gebildeten Hydroperoxyde, zu drei optisch aktiven Allylalkoholen: ()-Caren-(2)-trans-ol-(4) (2), (+)-Caren-(4)-trans-ol-(3) (3) und ()-Caren-[4(10)]-trans-ol-(3) (4) im Verhältnis von etwa 2:1:1. – Ebenso wie beim α-Pinen erfolgt auch beim Caren-(3) der Eintritt des Sauerstoffs ausschließlich auf derjenigen Seite des Moleküls, die von der raumerfüllenden Isopropylidengruppe abgewandt ist. Während α-Pinen nur das trans-Pinocarveol liefert, werden bei Caren-(3) sämtliche trans-Alkohole im angegebenen Verhältnis gefunden, die nach dem für die photosensibilisierte O2-Übertragung auf Olefine geltenden Prinzip der „indirekt substituierenden Addition in der Allylstellung” zu erwarten sind. Das Ausbleiben der entsprechenden cis-Allylhydroperoxyde bzw. cis-Allylalkohole wird mit der sterischen Abschirmung durch die Isopropylidengruppe erklärt.





Sur l'ar??me de viande de b?uf grill�e III. Pyrrolo [1,2-a]pyrazines, identification et synth�se

October 2004

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9 Reads

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15 Citations

Helvetica Chimica Acta

Synthesis of alkylpyrrolo[1,2‐ a ]pyrazines, roasted meat flavor constituents Seven alkylpyrrolo[1,2‐ a ]pyrazines have been identified for the first time in a roasted meat aroma obtained by thermolysis of the hydrosoluble flavor precursors of raw meat. Identification of individual components was done by capillary gas chromatography/mass spectroscopy coupling. The structure of these nitrogen heterocyclic compounds was for some time in doubt because of the similarity of the MS. with those of other diazaindene and diazanaphthalene derivatives such as benzimidazoles, indazoles, cyclopenta [ b ]pyrazines and dihydroquinoxalines. The structure of these new flavor components was completely elucidated in some cases by interpretation of NMR. spectra, the others being deduced by analogy. Hypotheses are formulated concerning the formation of this skeleton by a non‐enzymatic browning reaction between carbohydrates and amino acids. Four different schemes have been adopted to synthesize substituted isomers selectively.


Synthesis and Configuration of the Eight Diastereoisomeric Racemates of Dactyloxene‐B. The relative configuration of dactyloxene‐B and ‐C

October 2004

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18 Reads

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6 Citations

Helvetica Chimica Acta

The eight possible diastereoisomeric racemates of dactyloxene-B have been synthesized by a non-stereoselective route and their configurations and predominant conformations determined by 360-MHz-1H-NMR. and 90.5-MHz-13C-NMR. spectroscopy. Natural dactyloxene-B and -C are shown to have the relative configuration rel-(2R, 5R, 9S, 10R) and rel-(2R, 5S, 9S, 10R), respectively.



Citations (46)


... According to consumers, sweetness and aroma are the most significant contributing factors of fruit quality (2,3). The aroma of fruits is largely comprised of complex blend of VOCs (4). Large quantities of esters along with aldehydes and alcohols are responsible for its distinctive aroma of melons (5-7) and the peculiar aroma of melons is not associated with specific compound (3). ...

Reference:

Profiling of Volatile Compounds in Melons and Their Implication on Flavor, Aroma, Quality, and Food Safety
Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products
  • Citing Book
  • January 1979

Fortschritte der Chemie organischer Naturstoffe. Progress in the chemistry of organic natural products. Progrès dans la chimie des substances organiques naturelles

... For example, 3-mercapto-2-butanone (1), furfurylthiol (2), and 1-p-menthene-8-thiol (3), are key aroma components of meat, coffee, and grapefruit, respectively, and are required in order to imitate the original aromas of the targets (Figure 1). [1][2][3] In general, however, many sulfur-containing compounds have the drawback of instability. When a key aroma component undergoes chemical changes in flavouring composition, the impression of the flavour as a whole also changes. ...

ChemInform Abstract: 1-P-MENTHENE-8-THIOL: A POWERFUL FLAVOR IMPACT CONSTITUENT OF GRAPEFRUIT JUICE (CITRUS PARADISI MACFAYDEN)
  • Citing Article
  • March 1983

Chemischer Informationsdienst

... Murray and others (1972) , Parliment (1972) , and Winter and Kloti (1972) gave a fi rst insight into the complex mixture of aroma components of this tropical fruit. Degradation products of carotenoids (Demole et al. 1979 ;Naf et al. 1977 ;Whitfi eld et al. 1973 ;Winter et al. 1979a ), sulfur -containing components (Winter et al. 1976 ), and unusual aliphatic esters (Winter et al. 1979b ) were reported to play important roles in the unique and delicate fl avor of passion fruit. ...

ChemInform Abstract: MEGASTIGMA-5,8-DIEN-4-ONE, AN AROMA CONSTITUENT OF THE YELLOW PASSION FRUIT AND VIRGINIA TOBACCO
  • Citing Article
  • May 1979

Chemischer Informationsdienst

... Trinta e dois norterpenoides foram identificados nas variedades roxa e amarela (Whitfield & Last, 1986; Winterhalter, 1990) incluindo cetonas intensamente odoríferas como a β-ionona e β-damascenona (Casimir et al., 1981). Muitos éteres norterpenoides, os chamados edulanos (Murray et al.; Whitfield et al., 1973; Prestwich et al., 1976; Whitfield & Stanley, 1977; Whitfield & Sugowdz, 1979; Winter et al., 1979; Herderich & Winterhalter, 1991; Schmidt et al., 1995; Demole et al., 1979 ) e alguns hidrocarbonetos isoméricos, os megastigma- 4,6,8-trienos, os quais somente ocorrem na variedade roxa, são considerados a chave do " flavour " desta variedade (Murray et al., 1972; Whitfield & Sugowdz, 1979; Casimir et al., 1981). As pesquisas realizadas até o momento sobre os constituintes voláteis do maracujá restringem-se praticamente aos frutos. ...

ChemInform Abstract: AROMA CONSTITUENTS OF THE PURPLE PASSION FRUIT. TWO NEW EDULAN DERIVATIVES
  • Citing Article
  • May 1979

Chemischer Informationsdienst

... In our global fungal genome mining study, we discovered three types of onoceroids, which are triterpenoids synthesized from squalene or oxidosqualene through cyclization at both ends of the prenyl chain. Onoceroids have been isolated from bacteria 52 , ferns 53 , higher plants 54,55 , and animals 56 . However, to the best of our knowledge, onoceroids have never been isolated from fungi. ...

The Fragrance of Ambergris
  • Citing Chapter
  • December 1982

... It is interesting to note that among the non-terpenoid compounds, the oxacycloheptadec-8-en-2-one and hexadec-7-en-16-olide are not plant-synthesized substances, but are not uncommon in the animal kingdom as territory-marking compounds (e.g. from musk deer (Moschus moschiferus L.), civet cat (Viverra zibetha L.), and muskrat (Ondatra zibeticus L.) (Ohloff, 1994). Their frequent appearance in honey samples needs further investigation. ...

Animalic Compounds as Odorants
  • Citing Chapter
  • January 1994

... Natural musk was ®rst discovered in the exocrine scent glands of the deer-like Moschus animal Moschus moschiferus, which lives in the Himalayas. It functions as territorial marker and attracts the female counterpart (Walbaum, 1906;Ohloff, 1990). Since ca 1930, compounds with moschus (musk)like odor have been synthetically manufactured in large amounts and are used in fragrances for cosmetic and household products (Kevekordes et al., 1998). ...

Animalische Drogen Als Riechstoffe
  • Citing Chapter
  • January 1990

... 14 2-Acetylpyrrole and 2-formylpyrrole are the two most abundant and widely occurring pyrroles in foods. 15 2-Acetylpyrrole has a caramel-like odour while 2-formylpyrrole has a sweetcorn-like odour. The mechanism for www.soci.org ...

The role of heteroatomic substances in the aroma of foodstuffs
  • Citing Article
  • January 1979

Fortschritte der Chemie organischer Naturstoffe. Progress in the chemistry of organic natural products. Progrès dans la chimie des substances organiques naturelles

... The global approach is quite descriptive and is ineffective at explaining the mechanisms underlying the olfaction chain. Nevertheless, these studies can be helpful for flavorists and perfumers in search of new raw materials for the products they develop [32,[34][35][36][43][44][45][46]. The complete olfactory chain is complex and can lead to several biases. ...

Chemical Classification and Structure— Odour Relationships
  • Citing Chapter
  • January 1994

... Chiral alcohol 27 has been reported as a key intermediate for the synthesis of several natural and bioactive products. [55][56][57][58][59][60] Despite its apparent simplicity, its enantioselective synthesis relies on the use of stoichiometric chiral auxiliaries, [61][62] chiral pool strategies (i.e. enantiopure citronellene multistep transformation) [55][56] or Rucatalyzed hydrogenation at 100 bar dihydrogen pressure. ...

A Stereocontrolled Access to (±)-, (−)-, and (+)-Patchouli Alcohol
  • Citing Article
  • July 1981

Helvetica Chimica Acta