4-Methyl-2-(2-methyl-1-propenyl)tetrahydropyran (cis- and trans- mixture)

- CAS No.
- 16409-43-1
- Chemical Name:
- 4-Methyl-2-(2-methyl-1-propenyl)tetrahydropyran (cis- and trans- mixture)
- Synonyms
- ROSE OXIDE;2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-;(Z)-Rose oxide;ISOBUTENYL METHYLTETRAHYDROPYRAN;TETRAHYDRO-4-METHYL-2-(2-METHYL-1-PROPENYL)-2H-PYRAN;ROSE OXIDE RACEMIC;Rosoxide;FEMA 3236;rosenoxide;c-rose oxide
- CBNumber:
- CB5344138
- Molecular Formula:
- C10H18O
- Molecular Weight:
- 154.25
- MOL File:
- 16409-43-1.mol
- MSDS File:
- SDS
- Modify Date:
- 2025/1/27 9:38:02
Boiling point | 86 °C20 mm Hg(lit.) |
---|---|
Density | 0.873 g/mL at 20 °C(lit.) |
vapor pressure | 53Pa at 20℃ |
FEMA | 3236 | TETRAHYDRO-4-METHYL-2-(2-METHYLPROPEN-1-YL)PYRAN |
refractive index |
n |
Flash point | 157 °F |
storage temp. | under inert gas (nitrogen or Argon) at 2-8°C |
color | A colourless mobile liquid. |
Odor | at 1.00 % in dipropylene glycol. green red rose spicy fresh geranium |
Odor Type | floral |
optical activity | [α]20/D 28±1°, neat |
biological source | synthetic |
Water Solubility | 920mg/L at 20℃ |
JECFA Number | 1237 |
BRN | 1680588 |
LogP | 3.3 at 23℃ |
CAS DataBase Reference | 16409-43-1(CAS DataBase Reference) |
EPA Substance Registry System | 2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propenyl)- (16409-43-1) |
SAFETY
Risk and Safety Statements
Symbol(GHS) | ![]() GHS07 |
---|---|
Signal word | Warning |
Hazard statements | H315 |
Precautionary statements | P264-P280-P302+P352-P332+P313-P362+P364 |
Hazard Codes | Xi |
Risk Statements | 38-36/37/38 |
Safety Statements | 36-26 |
WGK Germany | 3 |
RTECS | UQ1470000 |
F | 10-23 |
HS Code | 29329990 |
Toxicity | The acute oral LD50 value in rats was reported as 4.3 g/kg (3.7-4.9 g/kg) and the acute dermal LD50 value in rabbits as > 5 g/kg (Moreno, 1973). |
4-Methyl-2-(2-methyl-1-propenyl)tetrahydropyran (cis- and trans- mixture) price More Price(6)
Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
---|---|---|---|---|---|---|---|
Sigma-Aldrich(India) | W323608 | Tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran mixture of cis and trans, ≥98%, stabilized, FG | 16409-43-1 | 1SAMPLE-K | ₹4990.33 | 2022-06-14 | Buy |
Sigma-Aldrich(India) | W323608 | Tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran mixture of cis and trans, ≥98%, stabilized, FG | 16409-43-1 | 100G | ₹7653.28 | 2022-06-14 | Buy |
Sigma-Aldrich(India) | W323608 | Tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran mixture of cis and trans, ≥98%, stabilized, FG | 16409-43-1 | 1KG | ₹21574.23 | 2022-06-14 | Buy |
Sigma-Aldrich(India) | 83917 | (−)-Rose oxide analytical standard | 16409-43-1 | 1ML | ₹3171.73 | 2022-06-14 | Buy |
Sigma-Aldrich(India) | 83915 | (+)-Rose oxide analytical standard | 16409-43-1 | 1ML | ₹9461.05 | 2022-06-14 | Buy |
4-Methyl-2-(2-methyl-1-propenyl)tetrahydropyran (cis- and trans- mixture) Chemical Properties,Uses,Production
Chemical Properties
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.
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.
4-Methyl-2-(2-methyl-1-propenyl)tetrahydropyran (cis- and trans- mixture) Preparation Products And Raw materials
Raw materials
1of2
chevron_rightPreparation Products
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Nagar Haveli Perfumes & Aromatics | +917506551149 | Mumbai, India | 230 | 58 | Inquiry |
Privi Speciality Chemicals Ltd. | +91-2233043500 +91-2233043500 | Mumbai, India | 63 | 58 | Inquiry |
Silverline Chemicals | +91-9810339289 +91-9810339289 | Haryana, India | 71 | 58 | Inquiry |
Suru Chemicals And Pharmaceuticals Pvt Ltd | +91-2267353637 +91-2267353637 | Maharashtra, India | 11 | 58 | Inquiry |
TCI Chemicals (India) Pvt. Ltd. | 1800 425 7889 | New Delhi, India | 6768 | 58 | Inquiry |
Crescent Fragrances Private Limited | 08048372305Ext 611 | GOA, India | 2 | 58 | Inquiry |
M A Aromas | 07942553282 | Mumbai, India | 26 | 58 | Inquiry |
Dee & Em Naturals & Fragrances | 08068442231Ext 350 | Karnataka, India | 5 | 58 | Inquiry |
Kalpsutra Chemicals Pvt. Ltd. | 91-22-21642085 | Maharashtra, India | 17 | 58 | Inquiry |
Arpan Aromatics | 08048372666Ext 828 | Ahmedabad, India | 138 | 58 | Inquiry |