16409-43-1 Usage
Description
FEMA 3236, also known as Rose Oxide, is a colorless liquid with a strong odor reminiscent of geranium and rose oil. It occurs in small quantities, mainly as the levorotatory cis form, in essential oils such as Bulgarian rose oil and geranium oil. Its chemical name is Tetrahydro-4-methyl-2-(2-methylpropen-1-yl)pyran, and it has a powerful distinctive geranium top note.
Uses
Used in Flavor and Fragrance Industry:
FEMA 3236 is used as a flavoring agent for its green, vegetative, and herbal taste with a citrus nuance at 20 ppm. It is also used as a fragrance ingredient to provide a distinctive geranium top note to various perfumes and scented products.
Used in Essential Oils:
FEMA 3236 is used in essential oils such as Bulgarian rose oil and geranium oil, where it occurs in small quantities. It contributes to the overall aroma and scent profile of these essential oils.
Used in Food and Beverage Industry:
FEMA 3236 can be used as a flavoring agent in the food and beverage industry to impart a unique taste and aroma to various products. Its green, vegetative, and herbal taste with a citrus nuance can be used to enhance the flavor of beverages, confectionery, and other food products.
Used in Cosmetics and Personal Care Products:
FEMA 3236 can be used in cosmetics and personal care products as a fragrance ingredient to provide a distinctive geranium and rose oil scent. It can be incorporated into products such as perfumes, body lotions, and shower gels to enhance their sensory properties.
Preparation
Rose oxide is usually prepared from citronellol, which can be converted into a
mixture of two allyl hydroperoxides by photosensitized oxidationwith singlet oxygen.
Reduction of the hydroperoxideswith sodium sulfite yields the corresponding
diols . Treatmentwith dilute sulfuric acid results in allylic rearrangement and
spontaneous cyclization of one of the isomers; amixture of diastereoisomeric rose
oxides is thus formed. The unreacted diol isomer is separated by distillation. (?)-
Citronellol as the starting material yields an approximately 7 : 3 mixture of (?)-cisand
(?)-trans-rose oxide. Higher proportions of the cis-isomer may be obtained
by dehydration with a stronger acid.Other methods for the production of rose oxide starting from citronellol consist
of halogenation–dehalogenation reactions of citronellol.An alternative technical process does not use citronellol but starts from prenal
[107-86-8] and 3-methyl-3-buten-1-ol [763-32-6]. Under acidic conditions,
the reaction affords a mixture of isomers of dehydro rose oxide (C10H16O6; [1786-
08-9], [92356-05-3], [60857-05-8]). Subsequent hydrogenation using a
ruthenium/alumina catalyst leads to rose oxide.The proportion of cis-isomer can
be increased by isomerization under acidic conditions.
Flammability and Explosibility
Nonflammable
Check Digit Verification of cas no
The CAS Registry Mumber 16409-43-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,4,0 and 9 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 16409-43:
(7*1)+(6*6)+(5*4)+(4*0)+(3*9)+(2*4)+(1*3)=101
101 % 10 = 1
So 16409-43-1 is a valid CAS Registry Number.
InChI:InChI=1/C10H18O/c1-8(2)6-10-7-9(3)4-5-11-10/h6,9-10H,4-5,7H2,1-3H3
16409-43-1Relevant articles and documents
Naves,Ochsner
, p. 397 (1962)
Palladium catalyzed oxidation of biorenewable β-citronellol and geraniol for the synthesis of polyfunctionalized fragrances
Venancio, Aldino N.,Menini, Luciano,Maronde, Daiane N.,Gusevskaya, Elena V.,Parreira, Luciana A.
, (2021/02/22)
β-Citronellol and geraniol are bio-renewable compounds found in essential oils of various plants. Allylic oxidation of trisubstituted sterically highly encumbered carbon-carbon double bonds in their molecules with dioxygen can be efficiently catalyzed by the palladium acetate/p-benzoquinone combination under 5?10 atm of dioxygen pressure without the need for conventionally used metal co-catalysts. Both substrates gave allyl acetates in ca. 90% combined yield. The oxidation of geraniol proceeded with excellent site-selectivity involving only one of its two C[dbnd]C bonds. Geraniol gave both linear and branched allyl acetates in comparable yields, whereas the reaction of β-citronellol showed high regioselectivity for the corresponding branched product. Polyfunctionalized oxygenated terpenes produced from β-citronellol and geraniol are of a potential importance as ingredients for fragrance compositions.
Comparative study of the vicinal functionalization of olefins with 2:1 bromide/bromate and iodide/iodate reagents
Agrawal, Manoj K.,Adimurthy, Subbarayappa,Ganguly, Bishwajit,Ghosh, Pushpito K.
experimental part, p. 2791 - 2797 (2009/08/08)
A comparative evaluation was made on the syntheses of vicinal halohydrins, halo methyl ethers, and halo acetates from olefins using 2:1 Br-/BrO3- and I-/IO3- reagents. In many cases both reagents afforded products selectively in high yields. The highest halogen atom efficiencies attained were 97% and 93% for Br-/BrO3- and I-/IO3-, respectively. Of the two reagents, I-/IO3- was established to be the preferred reagent for vicinal functionalization of linear alkenes and also for halo acetate preparation. However, only Br-/BrO3- was effective for vicinal functionalization of trans-stilbene and chalcones.
Aluminium triflate catalysed cyclisation of unsaturated alcohols: novel synthesis of rose oxide and analogues
Coulombel, Lydie,Weiwer, Michel,Dunach, Elisabet
experimental part, p. 5788 - 5795 (2010/03/03)
Aluminium trifluoromethanesulfonate was used as an efficient catalyst for the cycloisomerisation of several unsaturated alcohols into cyclic ethers such as rose oxide and some of its ether analogues.