936-92-5

Usage

Uses

Used in Food and Beverage Industry:
Rotundone is used as a flavor compound in the food and beverage industry, particularly in the production of wines. Its peppery aroma and taste enhance the overall sensory experience of the wine, making it an important ingredient in the creation of red wines.
Used in Fragrance Industry:
Due to its potent odorant properties and low detection threshold, rotundone can also be utilized in the fragrance industry to create unique and distinct scents for various products such as perfumes, colognes, and other scented items.
Used in Aromatherapy:
Rotundone's distinct peppery aroma can be employed in aromatherapy for its potential mood-enhancing and invigorating effects, contributing to a more relaxing and enjoyable experience for users.
Used in Research and Development:
The unique properties of rotundone make it an interesting compound for research and development in various fields, including the study of olfaction, flavor chemistry, and the development of new products in the food and beverage, fragrance, and aromatherapy industries.

Upstream product

• 33116-78-8 (1S,3R)-(+)-3-hydroxy-4-isocaranyl tosylate 
• 23957-97-3 (-)-(1S,3R,4R,6R)-4-bromo-3,7,7-trimethylbicyclo[4.1.0]heptan-3-ol 
• 498-15-7 (+)-Δ³-carene 
• 10395-46-7 1S,3R,4S,6R-(+)-3β,4β-caranediol 
• 22556-08-7 trans-3,4-caranediol 
• 498-15-7 Δ³-carene 
• 13466-78-9 3-carene 

Downstream Products

• 6617-28-3 phthalic acid mono-((1S,3S,4S)-caran-4-yl ester) 
• 4017-88-3 (+)-cis-caran-cis-4-ol 
• 4089-03-6 (1S,3S,4S)-caran-4-ol 
• 4176-04-9 (1R,4S,6S)-4,7,7-Trimethyl-bicyclo[4.1.0]heptan-3-one 
• 22339-03-3 3(10)-caren-4β-ol 
• 10395-46-7 1S,3R,4S,6R-(+)-3β,4β-caranediol 
• 4176-01-6 (-)-isocaranone 
• 24278-58-8 (+)-cis-4-caranone 
• 161906-32-7 p-Menth-4-en-1,2-diol 
• 10395-46-7 (+)-3α,4β-caranediol 
• 99-87-6 4-methylisopropylbenzene 
• 31507-62-7 3-Isopropyl-1-methyl-3-cyclopentenecarbaldehyde 
• 242127-32-8 (-)-p-Menth-4-en-2-one 
• 36482-69-6 (1R,4S,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one 

Relevant academic research and scientific papers

Carane amino alcohols as organocatalysts in asymmetric aldol reaction of isatin with acetone

Carane-derived β-amino alcohols with amino and hydroxy groups at positions 3 and 4 differing in their mutual arrangement and configuration were synthesized. Their application as organocatalysts in the asymmetric aldol reaction of isatin with acetone allowed one to obtain adducts with up to 84% enantiomeric excess.

Stereoselective Synthesis of Carane-Type Hydroxythiols and Disulfides Based on Them

Isomeric 10-sulfanylcaran-4-ols and 4-sulfanylcaran-3-ols were synthesized and used to prepare disulfides in high yields.

Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions - Synthesis of halohydrins and epoxides

β-Haloalkoxysulfonium ions generated by the reaction of electrogenerated Br+ and I+ ions stabilized by dimethyl sulfoxide (DMSO) reacted with sodium hydroxide and sodium methoxide to give the corresponding halohydrins and epoxides, respectively, whereas the treatment with triethylamine gave α-halocarbonyl compounds.

Synthesis of new enantiopure trans-3,4-diaminocaranes from (+)-3-carene

A synthetic strategy to obtain new enantiopure trans-3,4-diaminocaranes derived from (+)-3-carene via a stereoselective methodology is described. The stereoselective preparation of 3,4-α-carene- or 3,4-β-carene-epoxide is followed by a ring opening by sodium azide to obtain the azido-alcohols. Subsequent cyclization affords the corresponding aziridine diastereoisomers, which are converted to azido amines by opening of the aziridine rings by sodium azide and then reduced to the final diamine diastereoisomers. The absolute configurations of the final diamines and of novel intermediates are established by 1H NMR spectra correlated with conformational analysis supported by molecular modeling.

Syntheses of the optically active terpene hydroxyphenylselenides

The optically active hydroxyphenylselenides derived from the p-menthane, carane, and pinane systems have been obtained. Two methods of hydroxyphenylselenides synthesis have been compared. The first method is based on the reaction of alkenes with N-(phenylseleno)succinimide in the presence of water, and the second from epoxides as a result of the reaction with sodium benzeneselenolate. The influence of the substrate structures on the composition of the obtained products has been demonstrated.

Reaction of Alkenes with Hydrogen Peroxide and Sodium Iodide: A Nonenzymatic Biogenic-Like Approach to Iodohydrins

An efficient protocol to synthesize iodohydrins from alkenes is presented. Reactions were conducted in aqueous media using safe and readily available sodium iodide (the most abundant form of the element), and a highly convenient oxidant such as hydrogen peroxide. Addition of a protic acid triggers a faster and efficient process, a role formally related to that played by haloperoxidase enzymes in naturally occurring transformations. The successful application of these conditions to multigram scale preparations and over natural products derivatives is also discussed.

Diastereoselective epoxidation of olefins by organo sulfonic peracids, II

We have investigated the behaviour of sulfonic peracids 2 in situ generated towards olefins 7a, 7b, 9, 11, 14, 16, 18, allylic acid and homoallylic alcohols 20, 22, 24, 26, 28, 30, 33 and α,β-unsaturated ketones 35, 37, 39. Generally, the epoxidation proceeds in a peracid-like manner with greater diastereoselectivity than those by common oxidants. In particular, the epoxidation of Δ4 3-ketosteroids 39a-i led to 4α,5α-epoxides 40a-i with remarkable high de-values. Enhanced α-selectivity was also found in the epoxidation of cholesterol 28b. Due to the mild reaction conditions, even acid sensitive epoxides 8a, 8b, 10, 12, 13, 15, 17, 19 were obtained in good yields.

A NEW PARADIGM FOR ALKENE EPOXIDATION. ACTIVATION OF HYDROGEN PEROXIDE BY ORGANOPHOSPHORUS ELECTROPHILES

Diphenylphosphinic anhydride and certain other organophosphorus electrophiles mediate the high-yield conversion of alkenes to epoxides by hydrogen peroxide in buffered aqueous tetrahydrofuran.

Synthesis of naturally-occurring (-)-Δ9(12)-Capnellene and its antipode: An application of the photo-induced vinylcyclopropane-cyclopentene rearrangement

Abundantly available (+)-Δ3-Carene, 1 has been transformed into enantiomerically pure key intermediates viz. the enones (-)-7 and (+)-7, thus constituting a formal synthesis of both the enantiomers of Δ9(12)-Capnellene.