Ferulic Acid

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Ferulic acid, a phenolic compound abundant in rice bran, wheat, and the cell walls of many fruits, has catapulted from agricultural antioxidant to skin-care linchpin. Structurally, it boasts a 4-hydroxy-3-methoxycinnamic acid backbone with conjugated double bonds capable of donating an electron to neutralize free radicals while stabilizing its own resonance – a self-sacrificing superhero that doesn’t fall apart after the first punch.

Its most lauded feat: stabilizing vitamins C and E. Dr. Sheldon Pinnell’s oft-cited 2005 Journal of Investigative Dermatology study showed that adding 0.5-percent ferulic acid to 15-percent l-ascorbic acid and 1-percent α-tocopherol doubled photoprotection, as measured by sunburn-cell formation and erythema, and reduced vitamin C degradation by 50 percent over four months at room temperature. The acid’s planar structure nestles between ascorbic and tocopherol radicals, forming a resonance-stabilized network that resists oxidative collapse.

Beyond teamwork, ferulic acid alone inhibits tyrosinase, intercepts UV-generated cyclobutane pyrimidine dimers (DNA damage), and down-regulates MMP-1 expression in fibroblasts. Because it absorbs in both UVA and UVB ranges, Japan and EU regulators permit its use as a secondary natural UV filter up to 0.5 percent.

Formulation hurdles include limited water solubility and a propensity for oxidative browning if pH strays high. Ethoxydiglycol and propanediol serve as co-solvents, while microencapsulation in maltodextrin or silica microsponges enhances aesthetics, eliminating the coffee-stain hue that can show in high-dose serums.

In the bathroom, ferulic acid serums feel slightly viscous, often tinged amber. Apply in the a.m. under sunscreen; the antioxidant synergy extends SPF life and tackles visible-light radicals. Nighttime layering with retinoids poses no conflict and may further suppress MMP activity. Sensitive skin should patch test – the phenolic core can tingle – but most users acclimate quickly, finding ferulic-fortified serums the gold standard for daytime defense.

Ferulic Acid (Wikipedia)

Ferulic acid is a hydroxycinnamic acid derivative and a phenolic compound. It is an organic compound with the formula (CH3O)HOC6H3CH=CHCO2H. The name is derived from the genus Ferula, referring to the giant fennel (Ferula communis). Classified as a phenolic phytochemical, ferulic acid is an amber colored solid. Esters of ferulic acid are found in plant cell walls, covalently bonded to hemicellulose such as arabinoxylans. Salts and esters derived from ferulic acid are called ferulates.

Ferulic acid
Names
Preferred IUPAC name
(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
Other names
2-propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-
ferulic acid
3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid
3-(4-hydroxy-3-methoxyphenyl)acrylic acid
3-methoxy-4-hydroxycinnamic acid
4-hydroxy-3-methoxycinnamic acid
(2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid
Coniferic acid
trans-ferulic acid
(E)-ferulic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.892 Edit this at Wikidata
UNII
  • InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+ checkY
    Key: KSEBMYQBYZTDHS-HWKANZROSA-N checkY
  • InChI=1/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+
    Key: KSEBMYQBYZTDHS-HWKANZROBE
  • COc1cc(ccc1O)/C=C/C(=O)O
Properties
C10H10O4
Molar mass 194.186 g·mol−1
Appearance Crystalline powder
Melting point 168 to 172 °C (334 to 342 °F; 441 to 445 K)
0.78 g/L
Acidity (pKa) 4.61
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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