16409-43-1 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 16409-43-1 differently. You can refer to the following data:
1. Rose Oxide occurs in small quantities, mainly as the levorotatory
cis form, in essential oils (e.g., Bulgarian rose oil and geranium oil). Commercial
synthetic products are either optically active or inactive mixtures of the cis- and
trans-isomers. Their sensory properties depend on the starting material and the
method of synthesis.They are colorless liquids with a strong odor reminiscent
of geranium and rose oil.
2. Tetrahydro-4-methyl-2-(2-methylpropen-1-yl)pyran has a powerful distinctive geranium top note.
Occurrence
Reported found in the oils of rose (Bulgarian) and geranium (Réunion); both the cis- and the trans-form have been reportedly isolated from geranium oil. Unidentified isomers reported found in black currant berries, passion fruit, some types of Thymus and white wine.
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.
Taste threshold values
Taste characteristics at 20 ppm: green, vegetative and herbal with a citrus nuance.
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.
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.
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.
