Monocyclic monoterpene aldehyde

C10H14O, Mr 150.22, oil. Monocyclic monoterpene aldehyde occurring in both enantiomeric forms (/ )-(- )- and(S)-(-)-P.,bp. 104°C(900 Pa), [o]d 150.7°. LD50 (rat p. 0.) 2500 mg/kg. (-)-P. constitutes ca. 50% of Perilla oil from Perilla arguta and P. frutescens var. crispa (Lamiaceae), (+)-P. constitutes ca. 60% of the Philippine Sulpicia oil from Sulpicia orsuami and also occurs in Siler trilobum, Siam latifolium. Citrus reticulata, and other plants. The ( )-oxime of (5)-(-)-P. is used in Japan as a sweetener Perilla sugar and has a 2000-fold higher sweetness than saccharose. 

C,oH,40, Mr 150.22, bp. 72 C (4 hPa). A monocyclic monoterpene aldehyde. S. is the odor principle of saffron and is formed from the bitter saffron gluco-side picrocrocin [CisHjjO, Mr 330.38, mp. 156°C, [a]g -58° (H2O)]. S. acts as an androtermone, i.e., the substance determining the male gender of the green alga Chlamydomonas eugametus. S. occurs in saffron oil (Crocus sativus, Iridaceae) and is prepared from, e.g., citral. ... 

Citronellal is a monocyclic monoterpene aldehyde with high concentrations found in the essential oils of Corymbia citriodora, M. officinalis, and various Cymbopogon species. It is used for perfuming soaps and other products (Bornscheuer et al., 2014 O Neil, 2006). Only one study described biotransformation of citronellal in rabbits. Ishida et al. could isolate three neutral metabolites of (+)-citronellal in the urine of rabbits (Figure 9.11). An additional acidic metabolite was formed as the result of regioselective oxidation of the aldehyde and dimethyl allyl groups (Ishida et al., 1989). Based on animal data, metabolism of citronellal is also expected in humans. 

Biotransformation of Monoterpenoids by Microorganisms, Insects, and Mammals 14.3.2 Monocyclic Monoterpene Aldehyde... 

Monocyclic monoterpenes include the fully saturated menthol (5-methyl-2-isopropyl-cyclohexanol) (C6) (peppermint smell), the fully unsaturated analogue thymol (5-methyl-2-isopropylphenol) (G6) (smell of thyme) and the partially unsaturated a-terpinene (5,6-dihydro-4-isopropyltoluene) (G6) (lemon odour). Variants derive from different degrees of unsaturation and substitution and from different functional groups (e.g. alkyl, hydroxyl, aldehyde, peroxy and keto groups). 

Molecular structures of monoterpenoids are present as three major types acyclic, monocyclic and bicyclic. Oxygenated derivatives of acyclic monoterpenes are more widespread in nature than acyclic monoterpenes themselves. Such derivatives are the monoterpene alcohols citronellol and geraniol, or the monoterpene aldehydes citronellal and geranial. Mononocyclic monoterpene hydrocarbons are exemplified by limonene, which is a major component of orange and lemon peel oils, and p-phellandrene, which is emitted by conifer trees under biotic stress. These compounds are relatively common in nature. Bicyclic monoterpenes are represented by the aforementioned a-pinene, one of the most abundant and important monoterpenes. 

The monoterpenes are subdivided into three groups acyclic, monocyclic and bicyclic (there is only one tricyclic terpene tricyclene). Each group contains hydrocarbon terpenes, terpene alcohols, terpene aldehydes, ketones, oxides etc... 

Monoterpenoids are responsible for fragrances and flavors of many plants and thus their products are used in perfumery and as spices. To date over 1,500 monoterpenoids are known, and these constitute acyclic, monocyclic, and bicyclic monoterpenoids (32), which occur in nature as hydrocarbons, alcohols, aldehydes, and carboxylic acids and their esters. Several acyclic monoterpenoid hydrocarbons are known, and these include trienes such as 3-myrcene (Cl), a-myrcene (C2), (Z)-a-ocimene (C3), ( )-a-ocimene (C4), (Z)-3-ocimene (C5), and ( )-P-ocimene (C6). 3-Myrcene and 3-ocimene are constituents of basil (Oci-mum basilicum, Labiatae) and bay (Pimenta acris, Myrtaceae), pettitgrain (Citrus vulgaris, Rutaceae) leaves, strobiles of hops (Humulus lupulus, Cannabaceae), and several other essential oils. Unsaturated acyclic monoterpene alcohol constituents of plants and their derived aldehydes play a signihcant role in the perfume industry. Some common acyclic monoterpene alcohols and aldehydes include geraniol (C7), linalool (C8) (a... 

Monoterpenes (Cio) are the simplest members of the terpene series. They result from the condensation of two isoprene units and may be acyclic, monocyclic, bicyclic or tricyclic. The monoterpenes can have another functional moiety like alcohol (geraniol, linalool, menthol, bomeol), aldehyde (geranial, cihonellal), ketone (menthone, carvone, thujone), ester (bomyl acetate, linalyl acetate), ether (1,8-cineol) and phenol (thymol, carvacol). In the case of optically active molecules, the proportions of the enantiomers vary largely from one species to another. 

---