Available from stock

p-Coumaric acid

SKU: C0400

Category: Metabolites

Synonyms: para-Coumaric Acid , trans-p-Coumaric Acid , trans-4-Hydroxycinnamic acid , (E)-3-(4-Hydroxyphenyl)prop-2-enoic acid; 501-98-4
CAS-Number: C₉H₈O₃
Molecular Formula: 164.16
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥98% (HPLC)
Appearance: White to off-white powder
Identity: 1H-NMR

Properties

Solvents: ethanol (30 mg/ml), DMSO (15 mg/ml) or DMF (20 mg/ml).
Melting Point: 214 °C (decomp.)
Density: 1.329 (predicted)

Shipping: AMBIENT
Short Term Storage: +4°C
Long Term Storage: +4°C
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at +4°C.

Hazard statements: H315 - H319 - H335
Precautionary statements: P302 + P352 - P305 + P351 + P338
GHS Symbol: GHS07
Transportation: Not dangerous goods

Description: p-Coumaric acid is mainly a plant metabolite which exhibits antioxidant, antimicrobial, antitumor, antiangiogenic, antidiabetic, antihyperlipidemic, neuroprotective and anti-inflammatory properties. It shows bactericidal/quorum sensing activity by damaging bacterial cell membrane and by interacting with bacterial DNA. It prevents metabolic syndromes through the activation of brown adipose tissue (BAT), linked to UCP1 upregulation, with accelerated burning of fatty acids and glucose, leading to enhanced the energy expenditure and thermogenesis. Also used in proteomics, e.g. in western blot, p-coumaric is used as an enhancer in chemiluminescent substrates. Used in cosmetics as a skin-lightening compound, due to its antimelanogenic effects, based on its potent competitive inhibition of tyrosinase.
Smiles: OC1=CC=C(/C=C/C(O)=O)C=C1
InChi Key: NGSWKAQJJWESNS-ZZXKWVIFSA-N
References: (1) C. Luceri, et al., Br. J. Nutr. 97, 458 (2007) , (2) C. Haan & I. Behrmann, J. Immunol. Meth. 318, 11 (2007) , (3) S.F. Bodini, et al., Lett. Appl. Microbiol. 49, 551 (2009) , (4) D. Dolores & C.Y. Cheng, Spermatogenesis 1, 121 (2011) , (5) D. Stojkovic, et al., J. Sci. Food Agric. 93, 3205 (2013) , (6) S.J. Pragasam & M. Rasool, Inflamm. Res. 62, 489 (2013) , (7) S.J. Pragasam, et al., Inflammation 36, 169 (2013) , (8) C.S. Kong, et al., Phytother. Res. 27, 317 (2013) , (9) S. Shailasree, et al., Mol. Neurobiol. 51, 119 (2015) , (10) V. Amalan, et al., Biomed. Pharmacother. 84, 230 (2016) , (11) K. Pei, et al., J. Sci. Food Agric. 96, 2952 (2016) (Review) , (12) A. Abdel-Moneim, et al., Biomed. Pharmacother. 105, 1091 (2018) , (13) S.H. Sharma, et al., Chem. Biol. Interact. 291, 16 (2018) , (14) R. Sakamula, et al., Metab. Brain Dis. 33, 765 (2018) , (15) Y.C. Boo, Antioxidants 8, 275 (2019) (Review) , (16) X. Hu, et al., Front. Oncol. 10, 558414 (2020) , (17) X. Han, et al., FASEB J. 34, 7810 (2020) , (18) M.F. Abazari, et al., Mini Rev. Med. Chem. (epub ahead of print) (2021) (Review)
InChi: InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+

p-Coumaric acid is mainly a plant metabolite which exhibits antioxidant, antimicrobial, antitumor, antiangiogenic, antidiabetic, antihyperlipidemic, neuroprotective and anti-inflammatory properties. It shows bactericidal/quorum sensing activity by damaging bacterial cell membrane and by interacting with bacterial DNA. It prevents metabolic syndromes through the activation of brown adipose tissue (BAT), linked to UCP1 upregulation, with accelerated burning of fatty acids and glucose, leading to enhanced the energy expenditure and thermogenesis. Also used in proteomics, e.g. in western blot, p-coumaric is used as an enhancer in chemiluminescent substrates. Used in cosmetics as a skin-lightening compound, due to its antimelanogenic effects, based on its potent competitive inhibition of tyrosinase.

SKU: C0400 Category: Metabolites

Additional information

Additional information

Synonyms	para-Coumaric Acid, trans-p-Coumaric Acid, trans-4-Hydroxycinnamic acid, (E)-3-(4-Hydroxyphenyl)prop-2-enoic acid
Purity	≥98% (HPLC)
Appearance	White to off-white powder
CAS-Number	501-98-4
Molecular Formula	C9H8O3
Molecular Weight	164.16
Identity	1H-NMR
Solvents	ethanol (30 mg/ml), DMSO (15 mg/ml) or DMF (20 mg/ml).
Melting Point	214 °C (decomp.)
Density	1.329 (predicted)
Smiles	OC1=CC=C(/C=C/C(O)=O)C=C1
InChi Key	NGSWKAQJJWESNS-ZZXKWVIFSA-N
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	+4°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at +4°C.
Hazard statements	H315 – H319 – H335
Precautionary statements	P302 + P352 – P305 + P351 + P338
GHS Symbol	GHS07
Transportation	Not dangerous goods
References	(1) C. Luceri, et al., Br. J. Nutr. 97, 458 (2007), (2) C. Haan & I. Behrmann, J. Immunol. Meth. 318, 11 (2007), (3) S.F. Bodini, et al., Lett. Appl. Microbiol. 49, 551 (2009), (4) D. Dolores & C.Y. Cheng, Spermatogenesis 1, 121 (2011), (5) D. Stojkovic, et al., J. Sci. Food Agric. 93, 3205 (2013), (6) S.J. Pragasam & M. Rasool, Inflamm. Res. 62, 489 (2013), (7) S.J. Pragasam, et al., Inflammation 36, 169 (2013), (8) C.S. Kong, et al., Phytother. Res. 27, 317 (2013), (9) S. Shailasree, et al., Mol. Neurobiol. 51, 119 (2015), (10) V. Amalan, et al., Biomed. Pharmacother. 84, 230 (2016), (11) K. Pei, et al., J. Sci. Food Agric. 96, 2952 (2016) (Review), (12) A. Abdel-Moneim, et al., Biomed. Pharmacother. 105, 1091 (2018), (13) S.H. Sharma, et al., Chem. Biol. Interact. 291, 16 (2018), (14) R. Sakamula, et al., Metab. Brain Dis. 33, 765 (2018), (15) Y.C. Boo, Antioxidants 8, 275 (2019) (Review), (16) X. Hu, et al., Front. Oncol. 10, 558414 (2020), (17) X. Han, et al., FASEB J. 34, 7810 (2020), (18) M.F. Abazari, et al., Mini Rev. Med. Chem. (epub ahead of print) (2021) (Review)
InChi	InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+
Quantity	10 g, 25 g, Bulk