Sinapic acid

Names

[ CAS No. ]:
530-59-6

[ Name ]:
Sinapic acid

[Synonym ]:
4-Hydroxy-3,5-dimethoxycinnamic acid
2-Propenoic acid, 3-(4-hydroxy-3,5-dimethoxyphenyl)-, (E)-
Sinapic acid
3,5-Dimethoxy-4-hydroxycinnamic Acid
Sinapic acid, trans-
3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acid
3 5-dimethoxy-4-hydroxycinnamic acid
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acid
(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid
Sinapinic acid
2-propenoic acid, 3-(4-hydroxy-3,5-dimethoxyphenyl)-
3,5-DIMETHOXY-4-HYDROXY-TRANS-CINNAMIC ACID
(E)-sinapic acid
2-Propenoic acid, 3-(4-hydroxy-3,5-dimethoxyphenyl)-, (2E)-
EINECS 208-487-3
MFCD00004401
trans-3,5-Dimethoxy-4-hydroxycinnamic Acid
trans-sinapic acid

Biological Activity

[Description]:

Sinapinic acid (Sinapic acid) is a phenolic compound isolated from Hydnophytum formicarum Jack. Rhizome, acts as an inhibitor of HDAC, with an IC50 of 2.27 mM[1], and also inhibits ACE-I activity[2]. Sinapinic acid posssess potent anti-tumor activity, induces apoptosis of tumor cells[1]. Sinapinic acid shows antioxidant and antidiabetic activities[2]. Sinapinic acid reduces total cholesterol, triglyceride, and HOMA-IR index, and also normalizes some serum parameters of antioxidative abilities and oxidative damage in ovariectomized rats[3].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Angiotensin-converting Enzyme (ACE)

Research Areas >> Cancer

Research Areas >> Metabolic Disease

Natural Products >> Phenols

[Target]

HDAC:2.27 mM (IC50)

ACE-I

[In Vitro]

Sinapinic acid acts as an inhibitor of HDAC, with an IC50 of 2.27 mM[1]. Sinapinic acid also inhibits ACE-I activity[2]. Sinapinic acid inhibits HDAC activity in HeLa cells, suppresses the growth of HeLa and HT29 cells with IC50s of 0.91 ± 0.02 mM and 1.6 ± 0.02 mM at 72 h, respectively, induces apoptosis of these cancer cells[1].

[In Vivo]

Sinapinic acid (5 or 25 mg/kg, p.o. daily for 4 weeks) increases the serum estradiol concentration; decreases insulin resistance and the triglyceride and total cholesterol concentrations; and favorably affects the parameters of antioxidant abilities (reduces glutathione, superoxide dismutase) and oxidative damage in rats[3].

[References]

[1]. Senawong T, et al. Histone deacetylase (HDAC) inhibitory and antiproliferative activities of phenolic-rich extracts derived from the rhizome of Hydnophytum formicarum Jack.: sinapinic acid acts as HDAC inhibitor. BMC Complement Altern Med. 2013 Sep 22;13:232.

[2]. Quinn L, et al. Extraction and Quantification of Sinapinic Acid from Irish Rapeseed Meal and Assessment of Angiotensin-I Converting Enzyme (ACE-I) Inhibitory Activity. J Agric Food Chem. 2017 Aug 16;65(32):6886-6892.

[3]. Zych M, et al. The Effects of Sinapic Acid on the Development of Metabolic Disorders Induced by Estrogen Deficiency in Rats. Oxid Med Cell Longev. 2018 Jun 4;2018:9274246.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
403.4±40.0 °C at 760 mmHg

[ Melting Point ]:
203-205 °C (dec.)(lit.)

[ Molecular Formula ]:
C₁₁H₁₂O₅

[ Molecular Weight ]:
224.210

[ Flash Point ]:
158.6±20.8 °C

[ Exact Mass ]:
224.068466

[ PSA ]:
75.99000

[ LogP ]:
1.29

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.604

[ Stability ]:
Stable. Incompatible with strong oxidizing agents, strong bases. Combustible.

[ Water Solubility ]:
insoluble

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36-S37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2918990090

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2918990090

[ Summary ]:
2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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