Octinoxate - CAS 5466-77-3
Catalog number:
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
Molecular Weight:
Octinoxate is an organic compound that is an ingredient in some sunscreens and lip balms used in sunscreens and other cosmetics
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Clear Colorless Oil
octyl P-methoxycinnamate; 2-Ethylhexyl-p-methoxycinnamate; Octyl Methoxycinnamate;
Soluble in DMSO
Store at -20 °C
Quality Standard:
Enterprise Standard/USP
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Boiling Point:
198-200 ºC
Canonical SMILES:
1.UV absorption and photoisomerization of p-methoxycinnamate grafted silicone.
Pattanaargson S1, Hongchinnagorn N, Hirunsupachot P, Sritana-anant Y. Photochem Photobiol. 2004 Sep-Oct;80(2):322-5.
p-Methoxycinnamate moieties, UV-B-absorptive chromophores of the widely used UV-B filter, 2-ethylhexyl p-methoxycinnamate (OMC), were grafted onto the 7 mol% amino functionalized silicone polymer through amide linkages. Comparing with OMC, the resulting poly [3-(p-methoxycinnamido)(propyl)(methyl)-dimethyl] siloxane copolymer (CAS) showed less E to Z isomerization when exposed to UV-B light. The absorption profiles of the product showed the maximum absorption wavelength to be similar to that of OMC but with less sensitivity to the type of solvent. Poly (methylhydrosiloxane) grafted with 10 mol% p-methoxycinnamoyl moieties was prepared through hydrosilylations of 2-propenyl-p-methoxycinnamate, in which the resulting copolymer showed similar results to those of CAS.
2.Photostabilization of sunscreen oil through preparation of a free-flowing powder.
Latif R1, Refai H, Tawakkol S. J Microencapsul. 2011;28(3):159-65. doi: 10.3109/02652048.2010.520092.
Octyl-p-methoxycinnamate (OMC) is a sun-blocking agent that absorbs ultraviolet (UV) radiation in UVB range. However, when exposed to sunlight, OMC is converted into a less UV-absorbent form, which reduces its effectiveness. The aim of this study was to stabilize the oil by microencapsulation and to convert it into a free-flowing powder form. In addition, the study aimed to develop a suitable high-performance liquid chromatography method to detect the oil in the presence of its degradation product. OMC was microencapsulated by the congealable disperse-phase encapsulation using carnauba wax (cw) and beeswax (bw) at different wax-to-drug ratios (2:1 and 4:1). The photostability of the oil was investigated by exposing the microspheres to UV radiation. After 180 min of exposure, the photoprotective abilities of all the tested formulae were similar and reached about 82%. However, physicochemical assessment showed superiority of cw microspheres over their bw analogues.
3.Stability of octyl methoxycinnamate and identification of its photo-degradation product.
Pattanaargson S1, Limphong P. Int J Cosmet Sci. 2001 Jun;23(3):153-60. doi: 10.1046/j.1467-2494.2001.00071.x.
A stability study of octyl methoxycinnamate (OMC) using C-18 HPLC indicated that OMC degraded into a new product when exposed to sunlight. When kept in the dark at 4, 20, 32 and 60 degrees C for one month, no degradation of OMC was detected. Online HPLC-APCI-MS revealed similar APCI mass spectra for OMC and its degradation product. Isolation of the photo-degradation product was done using semi-preparative HPLC. NMR spectra of OMC and the isolated photo-degradation product indicated the change from an E-octyl-p-methoxycinnamate into a Z-octyl-p-methoxycinnamate. NMR spectra of the unfractionated-light-exposed-OMC showed that the Z-OMC was the only product generated.
4.Eco-friendly methodology for efficient synthesis and scale-up of 2-ethylhexyl-p-methoxycinnamate using Rhizopus oryzae lipase and its biological evaluation.
Kumar V1, Jahan F, Kameswaran K, Mahajan RV, Saxena RK. J Ind Microbiol Biotechnol. 2014 Jun;41(6):907-12. doi: 10.1007/s10295-014-1429-0. Epub 2014 Mar 26.
Lipase-mediated synthesis of phenolic acid esters is a green and economical alternative to current chemical methods. Octyl methoxycinnamate, an important UVB-absorbing compound, was synthesized by the esterification of p-methoxycinnamic acid with 2-ethyl hexanol using Rhizopus oryzae lipase. A molar ratio of 1:2 of p-methoxycinnamic acid and 2-ethyl hexanol was found to give an optimum yield using cyclo-octane (50 ml) as reaction solvent, at a temperature of 45 °C, and 750 U of lipase, resulting in a yield of 91.3 % in 96 h. This reaction was successfully scaled up to 400-ml reaction size where 88.6 %bioconversion was achieved. The synthesized compound was found to have superior antioxidant activity as compared to ascorbic acid. The synthesized compound also exhibited good antimicrobial activity against Escherichia coli, Klebsiella pneumonia, Salmonella typhi, Staphylococcus aures, Candida albicans (yeast), Aspergillus niger, Alternaria solani, and Fussarium oxysporum by well diffusion method in terms of zone of inhibitions (in mm).
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CAS 5466-77-3 Octinoxate

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