ChemicalBook > CAS DataBase List > 4-Methyl-2-(2-methyl-1-propenyl)tetrahydropyran (cis- and trans- mixture)

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

Product Name
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
Formula Weight
154.25
MOL File
16409-43-1.mol
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4-Methyl-2-(2-methyl-1-propenyl)tetrahydropyran (cis- and trans- mixture) Property

Boiling point:
86 °C20 mm Hg(lit.)
Density 
0.873 g/mL at 20 °C(lit.)
vapor pressure 
53Pa at 20℃
refractive index 
n20/D 1.454
FEMA 
3236 | TETRAHYDRO-4-METHYL-2-(2-METHYLPROPEN-1-YL)PYRAN
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
biological source
synthetic
optical activity
[α]20/D 28±1°, neat
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)
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Safety

Hazard Codes 
Xi
Risk Statements 
38-36/37/38
Safety Statements 
36-26
WGK Germany 
3
RTECS 
UQ1470000
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).
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
W323608
Product name
Tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2<I>H</I>-pyran
Purity
mixture of <I>cis</I> and <I>trans</I>, &#8805;98%, stabilized, FG
Packaging
1 unit
Price
$61.7
Updated
2025/07/31
Sigma-Aldrich
Product number
W323608
Product name
Tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2<I>H</I>-pyran
Purity
mixture of <I>cis</I> and <I>trans</I>, &#8805;98%, stabilized, FG
Packaging
1 unit
Price
$61.7
Updated
2025/07/31
Sigma-Aldrich
Product number
W323608
Product name
Tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran
Purity
mixture of cis and trans, ≥98%, stabilized, FG
Packaging
1kg
Price
$262
Updated
2025/07/31
Sigma-Aldrich
Product number
83917
Product name
(?)-Rose oxide
Purity
analytical standard
Packaging
1ml
Price
$59.5
Updated
2025/07/31
Sigma-Aldrich
Product number
W323608
Product name
Tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran
Purity
mixture of cis and trans, ≥98%, stabilized, FG
Packaging
100g
Price
$81.2
Updated
2023/01/07
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4-Methyl-2-(2-methyl-1-propenyl)tetrahydropyran (cis- and trans- mixture) Chemical Properties,Usage,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.

Chemical Properties

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.

Uses

Refer to the productμs Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Definition

ChEBI: Rose oxide is a member of the class of oxanes that is tetrahydro-2H-pyran which is substituted at positions 2 and 4 by an isoprop-1-enyl group and a methyl group, respectively. Organic compound of the pyran class and the monoterpene class and a fragrance found in roses and rose oil. All four possible stereoisomers are known; the 2S,4R and 2S,4S diastereoisomers [also known as the (-)-cis- and (-)-trans-isomers, respectively] are the main constituents in several essential oils and are used as a food flavouring and in perfumes and cosmetics. It has a role as a plant metabolite. It is a monoterpenoid, a member of oxanes and an olefinic compound.

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

Non flammable

4-Methyl-2-(2-methyl-1-propenyl)tetrahydropyran (cis- and trans- mixture) Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 4-Methyl-2-(2-methyl-1-propenyl)tetrahydropyran (cis- and trans- mixture) manufacturers

Hebei Chuanghai Biotechnology Co., Ltd
Product
FEMA 3236 16409-43-1
Price
US $1.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10 mt
Release date
2024-10-24
Hebei Chuanghai Biotechnology Co., Ltd
Product
(Z)-Rose oxide 16409-43-1
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2024-11-04
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Rose Oxide 16409-43-1
Price
US $99.00-35.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-16

16409-43-1, 4-Methyl-2-(2-methyl-1-propenyl)tetrahydropyran (cis- and trans- mixture)Related Search:


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