Tetrahydro-2-isobutyl-4-methylpyran-4-ol

Structural formula
Simplified structural formula without stereochemistry * = stereocenters
General
Surname	Tetrahydro-2-isobutyl-4-methylpyran-4-ol
other names	2-isobutyl-4-hydroxy-4-methyltetrahydropyran Florosa
Molecular formula	C 10 H 20 O 2
Brief description	colorless liquid with a floral odor
External identifiers / databases
CAS number 63500-71-0 65418-69-1 ( rel -2 R , 4 R ) 65418-70-4 ( rel -2 R , 4 S ) EC number 405-040-6 ECHA InfoCard 100.100.664 PubChem 3017432 ChemSpider 2285174 Wikidata Q27291866
properties
Molar mass	172.26 g mol −1
Physical state	liquid
density	0.948-0.955 g cm -3
Vapor pressure	0.01 hPa (20 ° C)
solubility	practically insoluble in water (23 mg l −1 at 23 ° C)
Refractive index	1.455-1.460
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution H and P phrases H: 319 P: ?
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Tetrahydro-2-isobutyl-4-methyl-pyran-4-ol is one chemically to the group of pyrans . It is produced industrially as a mixture of the cis and trans forms , which are each racemate . The technical product is thus a mixture of four stereoisomers.

Extraction and presentation

Tetrahydro-2-isobutyl-4-methylpyran-4-ol can be synthesized by the cyclocondensation of 3-methyl-3-buten-1-ol with 3-methylbutanal ; it is not a natural product.

properties

Tetrahydro-2-isobutyl-4-methylpyran-4-ol is a colorless liquid with a floral odor. It is very stable chemically.

use

Tetrahydro-2-isobutyl-4-methylpyran-4-ol is used as an odorous substance in cosmetics , including in perfumes .

Risk assessment

Tetrahydro-2-isobutyl-4-methylpyran-4-ol was included by the EU in 2012 in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of substance evaluation in the Community's ongoing action plan ( CoRAP ). The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. Ingestion of tetrahydro-2-isobutyl-4-methylpyran-4-ol was caused by concerns about its high risk characterization ratio (RCR) and widespread use. The re-evaluation took place from 2012 and was carried out by Spain . A final report was then published.

Individual evidence

1. ↑ ^{a b c d e f g} ECHA: Substance Evaluation Conclusion document for a mixture of: cis-tetrahydro-2-isobutyl-4-methylpyran-4-ol; trans-tetrahydro-2-isobutyl-4-methylpyran-4-ol , CoRAP , February 24, 2014, accessed December 27, 2019.
2. ↑ ^{a b c} Wiley-VCH: Ullmann's Food and Feed, 3 Volume Set . John Wiley & Sons, 2017, ISBN 978-3-527-33990-7 , pp. 1143 ( limited preview in Google Book search).
3. ↑ Entry on Tetrahydro-2-isobutyl-4-methylpyran-4-ol, mixed isomers (cis and trans) in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on May 29, 2018. Manufacturers or distributors can use the harmonized classification and labeling expand .
4. ^ AD Swift: Flavors and Fragrances . Elsevier, 1997, ISBN 978-1-84569-824-9 , pp. 30 ( limited preview in Google Book search).
5. ↑ Wolfgang Legrum: Fragrances, between stench and fragrance occurrence, properties and use of fragrances and their mixtures . Springer-Verlag, 2011, ISBN 978-3-8348-8276-9 , pp. 128 ( limited preview in Google Book search).
6. ↑ European Chemicals Agency (ECHA): Substance Evaluation Conclusion and Evaluation Report .
7. ↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): a mixture of: cistrahydro-2-isobutyl-4-methylpyran-4-ol, transtetrahydro-2-isobutyl-4-methylpyran-4-ol , accessed on 2 May 2020.