Identification of new volatile thiols in the aroma ofVitis vinifera L. var. Sauvignon blanc wines

Tominaga, Takatoshi; Furrer, Anton; Henry, Robert J.; Dubourdieu, Denis

doi:10.1002/(sici)1099-1026(199805/06)13:3<159::aid-ffj709>3.0.co;2-7

Cited by 331 publications

(304 citation statements)

References 6 publications

Supporting

Mentioning

297

Contrasting

Order By: Relevance

“…Various sulphur-containing compounds occur in wine and can contribute to a range of aromatic nuances, depending on the type of compound. Certain thiols typically contribute to the fruity characters of a wine, and attributes such as "grapefruit", "passion fruit", "box tree" and "gooseberry" have been used to describe the odour (Darriet et al, 1995;Tominaga et al, 1998a). These compounds are referred to as the volatile thiols.…”

Section: Volatile Thiolsmentioning

confidence: 99%

“…The volatile thiols playing an important role in Sauvignon blanc wine aroma are mainly 4-mercapto-4-methylpentan-2-one (4MMP), 3-mercaptohexan-1-ol (3MH) and 3-mercaptohexan-1-ol acetate (3MHA) (Darriet et al, 1995;Tominaga et al, 1996;Coetzee & Du Toit, 2012). Other volatile thiols have been identified; however, the concentration of these compounds in wines is usually below the perception threshold (Tominaga et al, 1998a).…”

Section: Volatile Thiolsmentioning

confidence: 99%

“…3MH has been described as "passion fruit", "grapefruit", "gooseberry" and "guava" (Swiegers et al, 2005;Nicolau et al, 2006;Van Wyngaard et al, 2014), with a perception threshold of 60 ng/L (Tominaga et al, 1998a), while 4MMP has been described as "box tree", "passion fruit", "broom" and "black current bud" (Darriet et al, 1995), with a perception threshold of 0.8 ng/L in a model wine solution (Tominaga et al, 1998a). The low perception thresholds reported makes these compounds potent aromatic contributors in wine.…”

Section: Volatile Thiolsmentioning

confidence: 99%

See 2 more Smart Citations

Sauvignon Blanc Wine: Contribution of Ageing and Oxygen on Aromatic and Non-aromatic Compounds and Sensory Composition : A Review

Coetzee

Toit

2015

SAJEV

View full text Add to dashboard Cite

Oxidation and the capacity for sufficient ageing potential of white wines are constant problems for winemakers worldwide. In general, it is accepted that certain grape varieties are especially sensitive to oxidation, suggesting that some of the chemical components key to their sensory attributes are strongly modulated by oxygen exposure. Sauvignon blanc is a well-documented example of an oxygen-sensitive wine, and understanding the stability of various compounds is crucial in order to preserve the fresh and fruity characters of Sauvignon blanc wines while preventing the formation of off-odours over a long period of time. Compounds such as the volatile thiols and methoxypyrazines are key aroma compounds responsible for the typical Sauvignon blanc aroma, while other aroma compounds, such as esters, alcohols and acids, can also contribute to the wine aroma. Oxidation-related compounds (such as aldehydes) can occur under certain conditions and it is essential to understand the chemistry behind oxidation to control and manage the development of various characteristics in wine. The sensory interactions occurring between various compounds (both aromatic and non-aromatic) are also important due to enhancing or suppressive effects that can mask certain aroma nuances. This review focuses on the stability of certain compounds of Sauvignon blanc wines during oxidation and ageing and how it affects the aromatic and non-aromatic composition of these wines. ABBREVIATIONS

show abstract

Section: Volatile Thiolsmentioning

confidence: 99%

Section: Volatile Thiolsmentioning

confidence: 99%

Section: Volatile Thiolsmentioning

confidence: 99%

See 1 more Smart Citation

Sauvignon Blanc Wine: Contribution of Ageing and Oxygen on Aromatic and Non-aromatic Compounds and Sensory Composition : A Review

Coetzee

Toit

2015

SAJEV

View full text Add to dashboard Cite

show abstract

“…The odour imparted to wine by these compounds has been defined as passion fruit, grapefruit, gooseberry and guava-type aromas (Coetzee & Du Toit, 2012;Van Wyngaardt et al, 2014). These volatile thiols are extremely potent, having perception thresholds of 60 ng/L for 3MH and 4 ng/L for 3MHA (Tominaga et al, 1996;1998). At excessive concentrations, these volatile thiols can impart strong, sweaty aromas reminiscent of cat's urine (Swiegers et al, 2009).…”

Section: Effect Of Skin Contact On the Chemical And Sensory Profile Omentioning

confidence: 99%

“…Another source of volatile thiols is from the conjugation of (E)-2-hexenal and certain sulphur compounds (Harsch et al, 2013). Research by Tominaga et al (1998) showed that the amplification of varietal aromas during fermentation occurs by the action of yeast carbon-sulphur lyases through an enzymatic mechanism that releases the volatile thiols. In another study, carried out by Swiegers et al (2006b), it was observed that 3MHA is formed from 3MH by the action of yeast acetyltransferases.…”

Section: Effect Of Skin Contact On the Chemical And Sensory Profile Omentioning

confidence: 99%

Effect of Skin Contact Before and During Alcoholic Fermentation on the Chemical and Sensory Profile of South African Chenin Blanc White Wines

Aleixandre-Tudó

Weightman

Panzeri

et al. 2015

SAJEV

View full text Add to dashboard Cite

The volatile and phenolic composition of Chenin blanc wines made with different skin contact treatments was studied. One batch of grapes was used to make a dry white wine according to two different treatments, namely pre-fermentative skin contact and complete fermentation on the skins. A white wine fermented without any skin contact was used as control. Fermentation on the skins and skin contact before fermentation led to significantly lower levels of terpenes, esters, acids and thiols, and the highest significant levels of alcohols and phenolic compounds. However, this effect was less pronounced in wines with skin contact before fermentation. Sensory analysis of all the experimental wines was also performed. The results showed a significant shift from the sensory attributes of fresh and tropical fruits of the control Chenin blanc wines towards riper fruit notes in the skin contact treatments. This observation was correlated with the length of the skin contact period. Possible reasons to explain the results observed in this study are discussed.

show abstract

1-Methoxyhexane-3-thiol, a Powerful Odorant of Clary Sage (Salvia sclarea L.)

Waal

Niclass

Snowden

et al. 2002

HCA

View full text Add to dashboard Cite

The peculiar and highly diffusive odor signal of flowering clary-sage plants (Salvia sclarea L.) was identified to derive from trace amounts of 1-methoxyhexane-3-thiol (1) by mass-spectrometry analysis and confirmed by comparison with synthetic racemic thiol (AE)-1. The enantiomers (S)-and (R)-1 were prepared by enantioselective synthesis, and the absolute configuration of (S)-1 was fully corroborated by X-ray-diffraction analysis of the crystalline thioester (1'S,1S)-2. Compound (S)-1 is one of the most powerful odorants known, with a detection threshold of 0.04 ¥ 10 À3 ng/l air, and is, with its herbaceous-green, alliaceous, and perspiration profile, key to the fragrance of clary-sage flowers and of the freshly distilled essential oil. As a consequence of its unique odor, 1 was also suspected to be part of the volatiles of a Ruta species where it was subsequently identified together with its homologue, 1-methoxyheptane-3-thiol (3), 1-methoxy-4-methylpentane-3-thiol (4), and the known 4-methoxy-2-methylbutane-2-thiol (5). The syntheses of (AE)-3 and (AE)-4 as well as of the enantiomer (R)-4 are described. In both natural fractions, the ratio (S)-1/(R)-1 was slightly in favor of the (S)-enantiomer. Natural 4 has (R)-configuration.1. Introduction. ± Clary-sage (Salvia sclarea L.) fields in full blossom elicit a peculiar olfactory signal, both intriguing and repulsive, somewhat reminiscent of human axillary perspiration, and very distinct from the array of odors known and available to a perfumer in industry. Always attracted by novel and original scents, we became interested in this highly unusual top note. In a recent monograph on sage oils [1], Boelens and Boelens state that −fresh plant material of Salvia sclarea has a strong, pungent and penetrating odor that is often disliked. This odor disappears during steam distillation and can not be recognized as the essential oil×. The monograph cites numerous references that report chemical and sensory evaluation of sage oils. Notably, Maurer and Hauser identified more than 250 chemical constituents in clary-sage oil (S. sclarea L.) [2a], but none of them is responsible for the pungent top notes [2b].Serendipity brought us into contact with local farmers who cultivate clary sage for essential-oil production. When gently rubbing the flower panicles on a hot summer evening prior to harvest, the odor signal was strong and unambiguously recognized. The aqueous forerun from steam distillation of freshly cut aerial plant material produced a fraction which allowed isolation and identification of the target compound, 1-methoxyhexane-3-thiol (1), after a series of focussed separation steps combined with mass spectrometry and comparison with synthetic reference materials.In this communication, we describe the isolation and identification of 1-methoxyhexane-3-thiol (1) as a new impact odorant from a steam distillate of S. sclarea L. The synthesis of racemic thiol (AE)-1 and its enantiomers is presented,

show abstract

Identification of new volatile thiols in the aroma ofVitis vinifera L. var. Sauvignon blanc wines

Cited by 331 publications

References 6 publications

Sauvignon Blanc Wine: Contribution of Ageing and Oxygen on Aromatic and Non-aromatic Compounds and Sensory Composition : A Review

Sauvignon Blanc Wine: Contribution of Ageing and Oxygen on Aromatic and Non-aromatic Compounds and Sensory Composition : A Review

Effect of Skin Contact Before and During Alcoholic Fermentation on the Chemical and Sensory Profile of South African Chenin Blanc White Wines

1-Methoxyhexane-3-thiol, a Powerful Odorant of Clary Sage (Salvia sclarea L.)

Contact Info

Product

Resources

About