(R)-octinoxate

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for (R)-octinoxate are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the (R)-octinoxate?

The molecule (R)-octinoxate presents a molecular formula of C18H26O3 and its IUPAC name is [(2R)-2-ethylhexyl] (E)-3-(4-methoxyphenyl)prop-2-enoate.

(R)-Octinoxate is a molecule used in sunscreen and cosmetics as an ultraviolet light absorber. It is a derivative of 2-ethylhexanol. Octinoxate is the ester of 2-ethylhexanoic acid and 2-methoxyethanol. It is a clear to pale yellow liquid with a faint odor. Octinoxate is insoluble in water but soluble in most organic solvents..

Octinoxate is used in sunscreen formulations to absorb ultraviolet light. It is also used as a plasticizer and stabilizer in cosmetics. Octinoxate is used in combination with other sunscreen ingredients such as titanium dioxide and zinc oxide..

The safety of octinoxate has been questioned by some studies. Octinoxate has been shown to be an endocrine disruptor in animals. Octinoxate has also been shown to be a photo-allergen in some people..

3D structure

Cartesian coordinates

Geometry of (R)-octinoxate in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

(R)-octinoxate YBGZDTIWKVFICR-NRMKIYEFSA-N chemical compound 2D structure molecule svg
(R)-octinoxate

 

Molecule descriptors

 
IUPAC name[(2R)-2-ethylhexyl] (E)-3-(4-methoxyphenyl)prop-2-enoate
InChI codeInChI=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+/t15-/m1/s1
InChI KeyYBGZDTIWKVFICR-NRMKIYEFSA-N
SMILESCCCC[C@@H](CC)COC(=O)/C=C/c1ccc(OC)cc1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (R)-octinoxate
  • 2-PROPENOIC ACID, 3-(4-METHOXYPHENYL)-, 2-ETHYLHEXYL ESTER, (2E)-, (R)-
  • AB01563303_01
  • CCG-213327
  • OCTINOXATE, (R)-
  • Q27290927
  • U8YHQ4ME6H

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1633887

Physico-Chemical properties

IUPAC name[(2R)-2-ethylhexyl] (E)-3-(4-methoxyphenyl)prop-2-enoate
Molecular formulaC18H26O3
Molecular weight290.397
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity87.57
LogP4.5
Topological polar surface area35.5

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.