2-Ethylhexyl 4-Methoxycinnamate - 10mM in DMSO , CAS No.5466-77-3

CAS: 5466-77-3 Cat. No.: E424656 Molecular Weight: 290.4 Beilstein Registry Number: 5946630 EC Number: 226-775-7

GRADE & PURITY 10mM in DMSO

Synonyms

Octinoxate|5466-77-3|83834-59-7|2-Ethylhexyl 4-methoxycinnamate|Parsol MCX|Parsol MOX|Parsol|2-Ethylhexyl-p-methoxycinnamate|2-Ethylhexyl p-methoxycinnamate|4-Methoxycinnamic Acid 2-Ethylhexyl Ester|Octyl methoxycinnamate|Escalol 557|2-Ethylhexyl trans-4-

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

OMC can prevent the formation of UV induced cyclobutane pyrimidine dimer (CDP) by filtering UVB

Specifications

Synonyms

Octinoxate | 5466-77-3 | 83834-59-7 | 2-Ethylhexyl 4-methoxycinnamate | Parsol MCX | Parsol MOX | Parsol | 2-Ethylhexyl-p-methoxycinnamate | 2-Ethylhexyl p-methoxycinnamate | 4-Methoxycinnamic Acid 2-Ethylhexyl Ester | Octyl methoxycinnamate | Escalol 557 | 2-Ethylhexyl trans-4-

Specifications & Purity

10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Names and Identifiers

• Canonical Smiles: CCCCC(CC)COC(=O)C=CC1=CC=C(C=C1)OC
• IUPAC Name: 2-ethylhexyl (E)-3-(4-methoxyphenyl)prop-2-enoate
• InChIKey: YBGZDTIWKVFICR-JLHYYAGUSA-N
• INCHI: 1S/C18H26O3/c1-4-6-7-15(5-2)14-21-18(19)13-10-16-8-11-17(20-3)12-9-16/h8-13,15H,4-7,14H2,1-3H3/b13-10+
• Isomeric SMILES: CCCCC(CC)COC(=O)/C=C/C1=CC=C(C=C1)OC
• RTECS: UD3392732
• Molecular Weight: 290.4
• Beilstein: 5946630
• Reaxy-Rn: 5946632
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=5946632&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Cinnamic acids and derivatives
      • Subclass Cinnamic acid esters

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Cinnamic acids and derivatives
• Subclass: Cinnamic acid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Cinnamic acid esters
• Alternative Parents: Styrenes Phenoxy compounds Methoxybenzenes Anisoles Fatty acid esters Alkyl aryl ethers Enoate esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Cinnamic acid ester - Phenoxy compound - Anisole - Methoxybenzene - Phenol ether - Styrene - Alkyl aryl ether - Fatty acid ester - Monocyclic benzene moiety - Fatty acyl - Benzenoid - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Carboxylic acid ester - Monocarboxylic acid or derivatives - Ether - Carboxylic acid derivative - Organic oxide - Organooxygen compound - Hydrocarbon derivative - Carbonyl group - Organic oxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

Discover Target: EHMT2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Light sensitive.
• Refractive Index: 1.55
• Flash Point(°F): 379.4 °F
• Flash Point(°C): 193°C(lit.)
• Molecular Weight: 290.400 g/mol
• XLogP3: 5.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 290.188 Da
• Monoisotopic Mass: 290.188 Da
• Topological Polar Surface Area: 35.500 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 304.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Chuntao Xu, Xuemin Zeng, Zujin Yang, Hongbing Ji.  (2021)  Sunscreen Enhancement of Octyl Methoxycinnamate Microcapsules by Using Two Biopolymers as Wall Materials.  Polymers,  13  (6): (866).  [PMID:33799764] [10.3390/polym13060866]

2. Yijie Zhou, Yong Qian, Jingyu Wang, Xueqing Qiu, Hongbo Zeng.  (2020)  Bioinspired Lignin-Polydopamine Nanocapsules with Strong Bioadhesion for Long-Acting and High-Performance Natural Sunscreens.  BIOMACROMOLECULES,      [PMID:32662631] [10.1021/acs.biomac.0c00696]

3. Guifeng Liu, Huan Liu, Yuanjun Tong, Linyan Xu, Yu-Xin Ye, Cheng Wen, Ningbo Zhou, Jianqiao Xu, Gangfeng Ouyang.  (2020)  Headspace solid-phase microextraction of semi-volatile ultraviolet filters based on a superhydrophobic metal-organic framework stable in high-temperature steam.  TALANTA,      [PMID:32887097] [10.1016/j.talanta.2020.121175]

4. Lixian Xu, Di Wu, Bingrong Zhou, Yang Xu, Wenjuan Wang, Dinghua Yu, Dan Luo.  (2018)  Microencapsulated sunblock nanoparticles based on zeolitic imidazole frameworks for safe and effective UV protection.  RSC Advances,  8  (22): (12315-12321).  [PMID:35539407] [10.1039/C8RA00632F]

5. Qingqing Yu, Gongyuan Wang, Zhihao Shao, Yunfei Sun, Zhou Yang.  (2024)  Changes in life history parameters and expression of key genes of Brachionus plicatilis exposed to a combination of organic and inorganic ultraviolet filters.  CHEMOSPHERE,      [PMID:38697570] [10.1016/j.chemosphere.2024.142213]