71617-10-2

Basic information

• Product Name: ISOPENTYL-4-METHOXYCINNAMATE
• Synonyms: 3-(4-methoxyphenyl)-2-propenoicaci3-methylbutylester;3-(4-methoxyphenyl)-2-propenoicacid3-methylbutylester;3-Methylbutyl3-(4-methoxyphenyl)-2-propenoate;Isoamylp-methoxycinnamate;neoheltopane1000;isopentyl p-methoxycinnamate;Isoamyl 4-methoxycinnamate;Amyl P-Methoxy Cinnamate
• CAS NO: 71617-10-2
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32
• EINECS: 275-702-5
• Product Categories: Aromatic Cinnamic Acids, Esters and Derivatives;Cinnamic acid;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 71617-10-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 158°C/0.7mmHg(lit.)
• Flash Point: 151.6 °C
• Appearance: /
• Density: 1.031 g/cm³
• Vapor Pressure: 1.89E-05mmHg at 25°C
• Refractive Index: 1.5560 to 1.5600
• Water Solubility: 2.47mg/L at 20℃
• BRN: 3132627
• CAS DataBase Reference: ISOPENTYL-4-METHOXYCINNAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: ISOPENTYL-4-METHOXYCINNAMATE(71617-10-2)
• EPA Substance Registry System: ISOPENTYL-4-METHOXYCINNAMATE(71617-10-2)

Safety Data

• WGK Germany: 2
• RTECS: UD3393500
• Hazardous Substances Data: 71617-10-2(Hazardous Substances Data)

Usage

Description

ISOPENTYL-4-METHOXYCINNAMATE, also known as Isoamyl 4-Methoxycinnamate, is a chemical compound commonly used in the cosmetic industry. It is an organic compound with the molecular formula C18H22O3 and is characterized by its ability to absorb ultraviolet (UV) radiation, making it an effective ingredient in sunscreen formulations.

Uses

Used in Cosmetic Industry:
ISOPENTYL-4-METHOXYCINNAMATE is used as an active ingredient in sunscreens for its protective properties against harmful UVA and UVB rays. It is valued for its ability to provide broad-spectrum protection, helping to prevent sunburn, premature skin aging, and reducing the risk of skin cancer caused by excessive sun exposure.
Used in Sunscreen Compositions:
ISOPENTYL-4-METHOXYCINNAMATE is used as a UV filter in highly protective sunscreen compositions. It is particularly effective in absorbing both UVA and UVB radiation, offering a high level of protection to the skin. ISOPENTYL-4-METHOXYCINNAMATE is also known for its photostability, meaning it maintains its protective properties even after prolonged sun exposure.
Brand Name:
The brand name for ISOPENTYL-4-METHOXYCINNAMATE is Neo Heliopan, manufactured by H & R Florasynth. It was previously known as Isoamyl Methoxycinnamate, and the International Cosmetic Ingredient (INCI) name for this compound is isoamyl p-methoxycinnamate.

InChI:InChI=1/C15H20O3/c1-12(2)10-11-18-15(16)9-6-13-4-7-14(17-3)8-5-13/h4-9,12H,10-11H2,1-3H3/b9-6+

Synthetic route

i-Amyl alcohol (123-51-3) + ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate (24393-56-4) → isoamyl p-methoxycinnamate (71617-10-2)

Conditions	Yield
With toluene-4-sulfonic acid Heating;	89%

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate (24393-56-4) + sodium isopentoxide (19533-24-5) → isoamyl p-methoxycinnamate (71617-10-2)

Conditions	Yield
With i-Amyl alcohol Entfernen des entstehenden Aethanols;

4-methoxy-benzaldehyde (123-11-5) + α-hydrazino-phenylacetic acid → isoamyl p-methoxycinnamate (71617-10-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 99 percent / 4-(dimethylamino)pyridine / dimethylformamide / 25 °C 2: 89 percent / p-TsOH / Heating View Scheme
Multi-step reaction with 2 steps 1: 97 percent / 4-(dimethylamino)pyridine; acetic acid; piperidine / dimethylformamide / 10 - 25 °C 2: 89 percent / p-TsOH / Heating View Scheme

isoamyl p-methoxycinnamate (71617-10-2) → (E)-3-[(1S,1aR,3aS,6R,6aR,6bR)-6-Hydroxy-6b-methoxy-1-(4-methoxy-phenyl)-2-oxo-1a,2,3a,6,6a,6b-hexahydro-1H-3-oxa-cyclobuta[cd]inden-5-yl]-acrylic acid 3-methyl-butyl ester + (1R,6S,7S,8R)-6-Methoxy-8-(4-methoxy-phenyl)-3-[(E)-2-(3-methyl-butoxycarbonyl)-vinyl]-bicyclo[4.2.0]octa-2,4-diene-7-carboxylic acid 3-methyl-butyl ester + (1R,7R,8R,9S)-7-Methoxy-9-(4-methoxy-phenyl)-4-[(E)-2-(3-methyl-butoxycarbonyl)-vinyl]-3-oxa-tricyclo[5.2.0.02,4]non-5-ene-8-carboxylic acid 3-methyl-butyl ester + C60H80O12 + cis 4-methoxycinnamic acid-3'-methylbutyl ester

Conditions	Yield
With oxygen Product distribution; Mechanism; multistep reaction: 1) irradiation, hexane;

isoamyl p-methoxycinnamate (71617-10-2) → (1R,6S,7S,8R)-6-Methoxy-8-(4-methoxy-phenyl)-3-[(E)-2-(3-methyl-butoxycarbonyl)-vinyl]-bicyclo[4.2.0]octa-2,4-diene-7-carboxylic acid 3-methyl-butyl ester + C60H80O12 + cis 4-methoxycinnamic acid-3'-methylbutyl ester

Conditions	Yield
In hexane Irradiation;

isoamyl p-methoxycinnamate (71617-10-2) → (E)-3-[(1S,1aR,3aS,6R,6aR,6bR)-6-Hydroxy-6b-methoxy-1-(4-methoxy-phenyl)-2-oxo-1a,2,3a,6,6a,6b-hexahydro-1H-3-oxa-cyclobuta[cd]inden-5-yl]-acrylic acid 3-methyl-butyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: hexane / Irradiation 2: air-oxygen View Scheme

isoamyl p-methoxycinnamate (71617-10-2) → (1R,7R,8R,9S)-7-Methoxy-9-(4-methoxy-phenyl)-4-[(E)-2-(3-methyl-butoxycarbonyl)-vinyl]-3-oxa-tricyclo[5.2.0.02,4]non-5-ene-8-carboxylic acid 3-methyl-butyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: hexane / Irradiation 2: air-oxygen View Scheme

Upstream product

• 4245-35-6 3-methylbutyl acrylate 
• 100-66-3 methoxybenzene 
• 1963-36-6 4-methoxycinnamaldehyde 
• 123-51-3 i-Amyl alcohol 
• 123-11-5 4-methoxy-benzaldehyde 
• 24393-56-4 ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate 
• 19533-24-5 sodium isopentoxide 

Relevant articles and documents

S,O-Functionalized Metal-Organic Frameworks as Heterogeneous Single-Site Catalysts for the Oxidative Alkenylation of Arenes via C-H activation

Heterogeneous single-site catalysts can combine the precise active site design of organometallic complexes with the efficient recovery of solid catalysts. Based on recent progress on homogeneous thioether ligands for Pd-catalyzed C-H activation reactions, we here develop a scalable metal-organic framework-based heterogeneous single-site catalyst containing S,O-moieties that increase the catalytic activity of Pd(II) for the oxidative alkenylation of arenes. The structure of the Pd?MOF-808-L1 catalyst was characterized in detail via solid-state nuclear magnetic resonance spectroscopy, N2 physisorption, and high-angle annular dark field scanning transmission electron microscopy, and the structure of the isolated palladium active sites could be identified by X-ray absorption spectroscopy. A turnover frequency (TOF) of 8.4 h-1 was reached after 1 h of reaction time, which was 3 times higher than the TOF of standard Pd(OAc)2, ranking Pd?MOF-808-L1 among the most active heterogeneous catalysts ever reported for the nondirected oxidative alkenylation of arenes. Finally, we showed that the single-site catalyst promotes the oxidative alkenylation of a broad range of electron-rich arenes, and the applicability of this heterogeneous system was demonstrated by the gram-scale synthesis of industrially relevant products.

A practical, efficient, and atom economic alternative to the Wittig and Horner-Wadsworth-Emmons reactions for the synthesis of (E)-α,β- unsaturated esters from aldehydes

We describe a highly efficient new methodology for the synthesis of (E)-α,β-unsaturated esters from aldehydes. In our DMAP-catalyzed reaction, both aromatic as well as aliphatic aldehydes furnish the desired products highly regio- and stereoselectively if treated with commercially available or synthetically easily accessible malonic acid half ester. A large scale application in the synthesis of p-methoxycinnamates, which are of use as sunscreen ingredients, is described.

Sulphonic acids and their use as UV absorbers

PCT No. PCT/EP96/04325 Sec. 371 Date Apr. 16, 1998 Sec. 102(e) Date Apr. 16, 1998 PCT Filed Oct. 4, 1996 PCT Pub. No. WO97/14680 PCT Pub. Date Apr. 24, 1997Sulphonic acids of formula (I) in which the components and indices have the meanings given in the description, are eminently suitable as u/v absorbers, especially in cosmetic sun-screening agents.