36431-72-8

Basic information

• Product Name: 2,6,10,10-Tetramethyl-1-oxaspiro[4.5]dec-6-ene
• Synonyms: 2,6,10,10-tetramethyl-1-oxaspiro[4.5]dec-6-en;FEMA 3774;2,6,10,10-TETRAMETHYL-1-OXASPIRO[4.5]DEC-6-ENE;2,6,10,10-TETRAMETHYL-1-OXASPIROL[4,5]DEC-6-ENE;spiroxide;THEASPIRAN;(+/-)-THEASPIRANE;THEASPIRANE
• CAS NO: 36431-72-8
• Molecular Formula: C₁₃H₂₂O
• Molecular Weight: 194.31
• EINECS: 253-031-9
• Product Categories: Flavor;C12 to C20+;Building Blocks;Chemical Synthesis;Furans;Heterocyclic Building Blocks
• Mol File: 36431-72-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 68-72 °C3 mm Hg(lit.)
• Flash Point: 195 °F
• Appearance: /
• Density: 0.931 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0281mmHg at 25°C
• Refractive Index: n20/D 1.438(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• BRN: 1424383
• CAS DataBase Reference: 2,6,10,10-Tetramethyl-1-oxaspiro[4.5]dec-6-ene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6,10,10-Tetramethyl-1-oxaspiro[4.5]dec-6-ene(36431-72-8)
• EPA Substance Registry System: 2,6,10,10-Tetramethyl-1-oxaspiro[4.5]dec-6-ene(36431-72-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 2
• Hazardous Substances Data: 36431-72-8(Hazardous Substances Data)

Usage

Description

2,6,10,10-Tetramethyl-1-oxaspiro[4.5]dec-6-ene, also known as Theaspirane, is a high-grade monomeric fragrance that is a pale yellow liquid. It is soluble in alcohol or propylene glycol and has a typical black tea aroma, sweet taste, and mixed aroma characteristics such as fruity and woody aromas. It is widely used internationally in the fragrance industry.

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

• 79421-96-8 4-(5-Chloro-2,2-dimethyl-6-methylene-cyclohexyl)-butan-2-ol 
• 446293-91-0 4-(2,6,6-trimethyl-cyclohex-1-enyl)-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 
• 113110-02-4 3-(3-hydroxy-butyl)-2,4,4-trimethyl-cyclohex-2-enol 
• 13720-37-1 dihydro-α-ionol 
• 57069-87-1 4-(6,6-Dimethyl-2-methylene-cyclohex-3-enyl)-butan-2-ol 

Downstream Products

• 65416-59-3 (2RS,5RS)-vitispirane 
• 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 
• 70788-30-6 (+/-)-(1'SR,6'RS)-1-(2,2,6-trimethylcyclohexyl)hexan-3-ol 

Relevant articles and documents

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.

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).