36431-72-8

Usage

Uses

Used in Fragrance Industry:
2,6,10,10-Tetramethyl-1-oxaspiro[4.5]dec-6-ene is used as a high-grade monomeric fragrance for its unique black tea aroma, sweet taste, and mixed aroma characteristics such as fruity and woody aromas. It is widely used in the fragrance industry to create various scent profiles for perfumes, cosmetics, and other scented products.

Characteristics

1. Found in tobacco leaves.2. Naturally present in yellow egg fruit, sweet-scented osmanthus, raspberry.3. The tea spiro in tobacco comes from the degradation of carotene.4. There are two isomers, one is woody, camphor aroma, and the other is naphthalene-like smell.

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 4637, 1985 DOI: 10.1016/S0040-4039(00)98772-0

Biochem/physiol Actions

Odor at 1.0%

InChI:InChI=1/C13H22O/c1-10-6-5-8-12(3,4)13(10)9-7-11(2)14-13/h6,11H,5,7-9H2,1-4H3

Upstream product

• 57069-87-1 4-(6,6-Dimethyl-2-methylene-cyclohex-3-enyl)-butan-2-ol 
• 13720-37-1 dihydro-α-ionol 
• 113110-02-4 3-(3-hydroxy-butyl)-2,4,4-trimethyl-cyclohex-2-enol 
• 446293-91-0 4-(2,6,6-trimethyl-cyclohex-1-enyl)-butan-2-ol 
• 79421-96-8 4-(5-Chloro-2,2-dimethyl-6-methylene-cyclohexyl)-butan-2-ol 
• 72008-46-9 4-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)butan-2-one 
• 17283-81-7 4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on 

Downstream Products

• 66965-89-7 (2R*,5S*)-2,6,10,10-Tetramethyl-1-oxaspiro<4.5>dec-6-en 
• 66965-88-6 (2R*,5R*)-2,6,10,10-Tetramethyl-1-oxaspiro<4.5>dec-6-en 
• 65416-59-3 (2RS,5RS)-vitispirane 
• 70788-30-6 (+/-)-(1'SR,6'RS)-1-(2,2,6-trimethylcyclohexyl)hexan-3-ol 

Relevant academic research and scientific papers

Amberlyst-15-catalyzed intramolecular S(N)2' oxaspirocyclization of secondary allylic alcohols. Application to the total synthesis of spirocyclic ethers theaspirane and theaspirone

A variety of substituted 1-oxaspiro[4.4]non-6-ene. 1-oxaspiro[4.5]dec-6- ene, 6-oxaspiro[4.5]dec-1-ene and 1-oxaspiro[5.5]undec-7-ene systems have been prepared by utilizing Amberlyst-15-catalyzed intramolecular S(N)2' oxaspirocyclizations of secondary allylic alcohols under mild reaction conditions in quantitative yields. This oxaspirocyclization was applied to the total synthesis of theaspirane and theaspirone from β-ionone in five steps. (C) 2000 Elsevier Science Ltd.

A NOVEL SELENIUM-MEDIATED SPIROANNELATION: ONE-STEP PREPARATION OF d1-THEASPIRANE FROM α-DIHYDROIONOL

dl-Theaspirane (1) was prepared by the selenium-mediated electrochemical oxidation of α-dihydroionol (2), via a novel selenium-mediated spiroannelation.

AN ELECTROCHEMICAL CHLORINATIVE ENE-TYPE REACTION OF ISOPRENOIDS

The chlorinative ene-type reaction of isoprenoids (12) has been performed by electrolysis in CH2Cl2-H2O-NaCl system.The reaction provides useful allylic chlorides 2 for terpene synthesis in high yields and is affected strikingly by the nature of halide ions and solvents. dl-Theaspirane 21 was prepared from α-dihydroionol via the electrolysis.

Isolation, tentative identification, and synthesis studies of the volatile components of the hairpencil secretion of the monarch butterfly

The major volatile components of the hairpencil secretion of the male monarch butterfly have been identified as benzyl caproate and either 1, 5, 5, 9-tetramethyl-10-oxabicyclo[4.4.0]-3- decen-2-one(1), or 2, 2, 6, 8-tetramethyl-7-oxabicyclo[4.4.0]-4-decen-3-one(2). One sequence designed to synthesize 1 yielded two isomeric products of structure 1 whose spectra are very similar to each other but distinctly different from those of the natural product; this sequence also yielded a tricyclic ketal (9). A second sequence gave two epimeric spiro compounds (12) and a third sequence gave a [4.3.0] ring system (14).

147. Model reactions for the biosynthesis of damascone-related compounds and their preparative application

We report a new general synthesis of damasconcs. In the presence of acids, 7, 8-dehydro-β-ionole (10) or the related diols 11 are converted into a mixture of β-damascone (2) and the 7, 8-dehydrotheaspiranes (19). In the same way the 6-hydroxy-7, 8-dehydro-α-ionoles 12 are transformed into a mixture of β-damascenone (3) and the 8-oxatheaspiranes (20). The reaction provides access to damascone derivatives 4-7 which have been found in nature. These synthetic experiments lend support to our hypotheses concerning the biogenesis of damascones from suitable carotenoids or their metabolites.