CAS 18374-76-0

(-)-Rotundone

Description:

(-)-Rotundone is a naturally occurring sesquiterpene that is primarily known for its distinctive aroma, often described as reminiscent of black pepper or spices. It is a colorless to pale yellow liquid at room temperature and is insoluble in water but soluble in organic solvents. The compound has garnered attention in the field of food science and oenology due to its role as a flavor compound in various wines, particularly those made from certain grape varieties. Its chemical structure features a bicyclic framework, contributing to its unique sensory properties. (-)-Rotundone is also noted for its low odor threshold, meaning that it can be detected at very low concentrations, making it a potent flavoring agent. Additionally, it has been studied for its potential biological activities, although further research is needed to fully understand its effects. Overall, (-)-Rotundone is significant not only for its sensory attributes but also for its potential applications in flavor enhancement and natural product chemistry.

Formula: C₁₅H₂₂O

InChI: InChI=1S/C15H22O/c1-9(2)12-6-5-10(3)15-13(8-12)11(4)7-14(15)16/h10-12H,1,5-8H2,2-4H3/t10-,11-,12+/m0/s1

InChI key: InChIKey=NUWMTBMCSQWPDG-SDDRHHMPSA-N

SMILES: O=C1C2=C(C[C@H](C(C)=C)CC[C@@H]2C)[C@@H](C)C1

Synonyms:

• Guaia-1(5),11-dien-2-one, (-)-
• 1(2H)-Azulenone, 3,4,5,6,7,8-hexahydro-3,8-dimethyl-5-(1-methylethenyl)-, (3S,5R,8S)-
• (-)-Rotundone
• (3S,5R,8S)-3,4,5,6,7,8-Hexahydro-3,8-dimethyl-5-(1-methylethenyl)-1(2H)-azulenone
• 1(2H)-Azulenone, 3,4,5,6,7,8-hexahydro-3,8-dimethyl-5-(1-methylethenyl)-, [3S-(3α,5α,8α)]-

(-)-Rotundone

CAS: 18374-76-0

Formula: C₁₅H₂₂O

Molecular weight: 218.34

Ref: 4Z-G-180005

Rotundone

CAS: 18374-76-0

Applications Rotundone is a sesquiterpene with a spicy, peppery aroma extracted from Cyperus rotundus. It is present in an Australian wine made from syrah (shiraz) grape.
References Gupta, V. V. S. R., et al.: Front. Microbiol., 10, (2019)

Formula: C₁₅H₂₂O

Color and Shape: Neat

Molecular weight: 218.335

Ref: TR-R258745

Rotundone - 90%

CAS: 18374-76-0

Peppery aroma constituent of essential oil of Cyperus rotundus (nutgrass)

Formula: C₁₅H₂₂O

Purity: Min. 95%

Molecular weight: 218.33 g/mol

Ref: 3D-XR175543

Rotundone - 30%

CAS: 18374-76-0

Peppery aroma constituent of essential oil of Cyperus rotundus (nutgrass)

Formula: C₁₅H₂₂O

Purity: Min. 95%

Molecular weight: 218.33 g/mol

Ref: 3D-FR165899