Cinnamyl alcohol | CAS:104-54-1 | Manufacturer ChemFaces

Cinnamyl alcohol

ChemFaces products have been cited in many studies from excellent and top scientific journals

Product Name	Cinnamyl alcohol
Price:	$30 / 20mg
CAS No.:	104-54-1
Catalog No.:	CFN98119
Molecular Formula:	C₉H₁₀O
Molecular Weight:	134.18 g/mol
Purity:	>=98%
Type of Compound:	Phenylpropanoids
Physical Desc.:	Powder
Source:	The barks of Cinnamomum cassia Presl.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF Manual
Similar structural:	Comparison (Web) (SDF)
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Size /Price /Stock	10 mM * 1 mL in DMSO / $7.0 / In-stock
Other Packaging	*Packaging according to customer requirements(100uL/well, 200uL/well and more), and Container use Storage Tube With Screw Cap

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Description:

Cinnamyl alcohol could as a fragrance ingredient with no safety concerns, it readily autoxidizes upon air exposure, and forms strong sensitizers as determined by the local lymph node assay.

In vitro:

Contact Dermatitis. 2013 Mar;68(3):129-38.

Cinnamyl alcohol oxidizes rapidly upon air exposure.[Pubmed: 23421457]

Cinnamyl alcohol and cinnamal are frequent fragrance contact allergens. Both are included in the European baseline fragrance mix I, which is used for screening of contact allergy in dermatitis patients. The aim of this study was to investigate the autoxidation of Cinnamyl alcohol and to identify the oxidation products formed on air exposure. We also wanted to evaluate the effect of autoxidation on the sensitization potency of Cinnamyl alcohol.
METHODS AND RESULTS:
Samples of commercially available Cinnamyl alcohol with and without purification were exposed to air, and the autoxidation was followed by chemical analysis. The analysis was performed with mass spectrometry (LC/MS/MS). Sensitization potencies of compounds were determined with the murine local lymph node assay (LLNA) in mice. Chemical analysis showed that the concentration of Cinnamyl alcohol in the air-exposed samples decreased rapidly over time, and that autoxidation products were formed. Cinnamal, epoxy Cinnamyl alcohol and cinnamic acid were identified as oxidation products. According to our study, cinnamal and epoxy Cinnamyl alcohol were the first autoxidation products formed. The epoxy Cinnamyl alcohol was shown to be the oxidation product with the highest sensitization potency. The analysis of our samples of commercially available Cinnamyl alcohol showed that there was already a content of 1.5% cinnamal at the start of the autoxidation experiments.
CONCLUSIONS:
Cinnamyl alcohol readily autoxidizes upon air exposure, and forms strong sensitizers as determined by the LLNA. Cinnamal was formed in the largest amounts, showing that cinnamal is not only formed via bioactivation, as has previously been shown. A highly sensitizing epoxide was also identified and quantified in the oxidation mixture.

In vivo:

Food Chem Toxicol. 2007;45 Suppl 1:S1-23.

A toxicologic and dermatologic assessment of related esters and alcohols of cinnamic acid and cinnamyl alcohol when used as fragrance ingredients.[Pubmed: 18035463 ]

A toxicologic and dermatologic assessment of related esters and alcohols of cinnamic acid and Cinnamyl alcohol when used as fragrance ingredients.

Cinnamyl alcohol Description

Source:	The barks of Cinnamomum cassia Presl.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Structure Identification:

Chemistry. 2014 Apr 25;20(18):5478-86.

Highly efficient direct aerobic oxidative esterification of cinnamyl alcohol with alkyl alcohols catalysed by gold nanoparticles incarcerated in a nanoporous polymer matrix: a tool for investigating the role of the polymer host.[Pubmed: 24644103]

METHODS AND RESULTS:
The selective aerobic oxidation of Cinnamyl alcohol to cinnamaldehyde, as well as direct oxidative esterification of this alcohol with primary and secondary aliphatic alcohols, were achieved with high chemoselectivity by using gold nanoparticles supported in a nanoporous semicrystalline multi-block copolymer matrix, which consisted of syndiotactic polystyrene-co-cis-1,4-polybutadiene. The cascade reaction that leads to the alkyl cinnamates occurs through two oxidation steps: the selective oxidation of Cinnamyl alcohol to cinnamaldehyde, followed by oxidation of the hemiacetal that results from the base-catalysed reaction of cinnamaldehyde with an aliphatic alcohol. The rate constants for the two steps were evaluated in the temperature range 10-45 °C. The Cinnamyl alcohol oxidation is faster than the oxidative esterification of cinnamaldehyde with methanol, ethanol, 2-propanol, 1-butanol, 1-hexanol or 1-octanol. The rate constants of the latter reaction are pseudo-zero order with respect to the aliphatic alcohol and decrease as the bulkiness of the alcohol is increased. The activation energy (Ea) for the two oxidation steps was calculated for esterification of Cinnamyl alcohol with 1-butanol (Ea = 57.8±11.5 and 62.7±16.7 kJ mol(-1) for the first and second step, respectively). The oxidative esterification of Cinnamyl alcohol with 2-phenylethanol follows pseudo-first-order kinetics with respect to 2-phenylethanol and is faster than observed for other alcohols because of fast diffusion of the aromatic alcohol in the crystalline phase of the support.
CONCLUSIONS:
The kinetic investigation allowed us to assess the role of the polymer support in the determination of both high activity and selectivity in the title reaction.

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Fragrance ingredients Compound Library Phenylpropanoids Compound Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	7.4527 mL	37.2634 mL	74.5268 mL	149.0535 mL	186.3169 mL
5 mM	1.4905 mL	7.4527 mL	14.9054 mL	29.8107 mL	37.2634 mL
10 mM	0.7453 mL	3.7263 mL	7.4527 mL	14.9054 mL	18.6317 mL
50 mM	0.1491 mL	0.7453 mL	1.4905 mL	2.9811 mL	3.7263 mL
100 mM	0.0745 mL	0.3726 mL	0.7453 mL	1.4905 mL	1.8632 mL

CFN99037	3-(4-Hydroxyphenyl)-1-propanol	10210-17-0	152.2	C₉H₁₂O₂
CFN96011	p-Coumaryl alcohol	3690-05-9	150.2	C₉H₁₀O₂
CFN89230	4-Methoxycinnamyl alcohol	53484-50-7	164.20	C₁₀H₁₂O₂
CFN92410	trans-3,4-Methylenedioxycinnamyl alcohol	58095-76-4	178.2	C₁₀H₁₀O₃
CFN97760	Coniferyl alcohol	32811-40-8	180.20	C₁₀H₁₂O₃
CFN96742	Dihydroconiferyl alcohol	2305-13-7	182.21	C₁₀H₁₄O₃
CFN96094	Gamma-Methoxyisoeugenol	63644-71-3	194.2	C₁₁H₁₄O₃
CFN96771	Acetylisoeugenol	93-29-8	206.24	C₁₂H₁₄O₃
CFN98088	beta-Hydroxypropiovanillone	2196-18-1	196.2	C₁₀H₁₂O₄
CFN94482	Dihydrosinapylalcohol	20736-25-8	212.24	C₁₁H₁₆O₄