Page last updated: 2024-12-11

rotundone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

rotundone: has a spicy aroma; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5321003
CHEBI ID191710
SCHEMBL ID180456
MeSH IDM0523299

Synonyms (17)

Synonym
rotundone
CHEBI:191710
18374-76-0
(3s,5r,8s)-3,8-dimethyl-5-prop-1-en-2-yl-3,4,5,6,7,8-hexahydro-2h-azulen-1-one
SCHEMBL180456
NUWMTBMCSQWPDG-SDDRHHMPSA-N
guaia-1(5),11-dien-2-one, (-)-
(-)-rotundone
(3s,5r,8s)-5-isopropenyl-3,8-dimethyl-3,4,5,6,7,8-hexahydro-1(2h)-azulenone
u33h52bq0p ,
fema no. 4867
3,8-dimethyl-5-prop-1-en-2-yl-3,4,5,6,7,8-hexahydro-2h-azulen-1-one, (3s,5r,8s)-
unii-u33h52bq0p
Q15424773
rotundone - 90%
XR175543
DTXSID301030485

Research Excerpts

Overview

Rotundone is an oxygenated sesquiterpene belonging to the family of guaianes. It gives the 'peppery' aroma to white and black pepper and to red wines.

ExcerptReferenceRelevance
"Rotundone is a sesquiterpene that gives grapes and wine a desirable 'peppery' aroma. "( Environmental Factors and Seasonality Affect the Concentration of Rotundone in Vitis vinifera L. cv. Shiraz Wine.
Barlow, EW; Fuentes, S; Herderich, M; Howell, K; Krstic, M; Zhang, P, 2015
)
2.1
"(-)-Rotundone is a potent odorant molecule with a characteristic spicy aroma existing in various plants including grapevines (Vitis vinifera). "( Cytochrome P450 CYP71BE5 in grapevine (Vitis vinifera) catalyzes the formation of the spicy aroma compound (-)-rotundone.
Ikoma, G; Kobayashi, H; Matsuo, H; Mochizuki, C; Saito, H; Sasaki, K; Shinmori, H; Shinohara, A; Suzuki, S; Takase, H; Takata, R, 2016
)
1.2
"Rotundone is an oxygenated sesquiterpene belonging to the family of guaianes, giving the 'peppery' aroma to white and black pepper and to red wines. "( Effective analysis of rotundone at below-threshold levels in red and white wines using solid-phase microextraction gas chromatography/tandem mass spectrometry.
Caputi, L; Carlin, S; Lanza, T; Mattivi, F; Minozzi, M; Nanni, D; Valenti, L; Vrhovsek, U, 2011
)
2.13

Effects

ExcerptReferenceRelevance
"Rotundone has an odor activity value in pepper on the order of 50000-250000 and is, on this criterion, by far the most powerful aroma compound yet found in that most important spice."( From wine to pepper: rotundone, an obscure sesquiterpene, is a potent spicy aroma compound.
Capone, DL; Eggers, M; Elsey, GM; Herderich, MJ; Krammer, G; Meier, M; Parker, M; Pollnitz, AP; Sefton, MA; Siebert, TE; Vössing, T; Widder, S; Wood, C, 2008
)
1.39
"Rotundone has an odor activity value in pepper on the order of 50000-250000 and is, on this criterion, by far the most powerful aroma compound yet found in that most important spice."( From wine to pepper: rotundone, an obscure sesquiterpene, is a potent spicy aroma compound.
Capone, DL; Eggers, M; Elsey, GM; Herderich, MJ; Krammer, G; Meier, M; Parker, M; Pollnitz, AP; Sefton, MA; Siebert, TE; Vössing, T; Widder, S; Wood, C, 2008
)
1.39
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
sesquiterpenoidAny terpenoid derived from a sesquiterpene. The term includes compounds in which the C15 skeleton of the parent sesquiterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl groups).
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (20)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (10.00)29.6817
2010's15 (75.00)24.3611
2020's3 (15.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 42.55

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index42.55 (24.57)
Research Supply Index3.04 (2.92)
Research Growth Index5.58 (4.65)
Search Engine Demand Index56.95 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (42.55)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (5.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other19 (95.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]