Sinapic acid

Modify Date: 2024-01-02 18:12:33

Sinapic acid Structure
Sinapic acid structure
 Common Name Sinapic acid
CAS Number 530-59-6 Molecular Weight 224.210
Density 1.3±0.1 g/cm3 Boiling Point 403.4±40.0 °C at 760 mmHg
Molecular Formula C11H12O5 Melting Point 203-205 °C (dec.)(lit.)
MSDS Chinese USA Flash Point 158.6±20.8 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Sinapic acid


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].

 Names

Name trans-sinapic acid
Synonym More Synonyms

 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
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.

 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

 Safety Information

Symbol GHS07
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

Malonic acid structure

Malonic acid

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Syringaldehyde structure

Syringaldehyde

CAS#:134-96-3

~%

Sinapic acid Structure

Sinapic acid

CAS#:530-59-6

Literature: Journal of the American Chemical Society, , vol. 70, p. 57
4-acetoxy-3,5-dimethoxybenzaldehyde structure

4-acetoxy-3,5-d...

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Sodium acetate structure

Sodium acetate

CAS#:127-09-3

Ethanoic anhydride structure

Ethanoic anhydride

CAS#:108-24-7

~%

Sinapic acid Structure

Sinapic acid

CAS#:530-59-6

Literature: EP1604643 A1, ; Page/Page column 10-11 ;
3-methyl-4-nitro-5-[2-(3,5-dimethoxy-4-hydroxyphenyl)ethenyl]isoxazole structure

3-methyl-4-nitr...

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~72%

Sinapic acid Structure

Sinapic acid

CAS#:530-59-6

Literature: Chimichi, Stefano; Sio, Francesco De; Donati, Donato; Fina, Giuseppe; Pepino, Roberto; Sarti-Fantoni, Piero Heterocycles, 1983 , vol. 20, # 2 p. 263 - 267
ethyl 3-(4-acetyloxy-3,5-dimethoxyphenyl)prop-2-enoate structure

ethyl 3-(4-acet...

CAS#:110233-74-4

~%

Sinapic acid Structure

Sinapic acid

CAS#:530-59-6

Literature: Phytochemistry (Elsevier), , vol. 12, p. 893 - 897
diazomethane structure

diazomethane

CAS#:186581-53-3

N/A structure

N/A

CAS#:1359001-20-9

~%

Sinapic acid Structure

Sinapic acid

CAS#:530-59-6

Methyl trans-3-(3,4,5-trimethoxyphenyl)acrylate structure

Methyl trans-3-...

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Literature: Chemistry and Biodiversity, , vol. 9, # 1 p. 91 - 98
alatanin 1 structure

alatanin 1

CAS#:131189-50-9

~%

N/A structure

N/A

CAS#:47845-44-3

Sinapic acid Structure

Sinapic acid

CAS#:530-59-6

Literature: Phytochemistry (Elsevier), , vol. 29, # 9 p. 2999 - 3001
Syringaldehyde structure

Syringaldehyde

CAS#:134-96-3

~%

Sinapic acid Structure

Sinapic acid

CAS#:530-59-6

Literature: Heterocycles, , vol. 20, # 2 p. 263 - 267
3-α-trans-sinapoyloxyjhanol 18-O-β-D-glucopyranoside structure

3-α-trans-sinap...

CAS#:1276682-51-9

~%

Sinapic acid Structure

Sinapic acid

CAS#:530-59-6

Literature: Journal of the Chinese Chemical Society, , vol. 56, # 6 p. 1186 - 1190

 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%

 Articles182

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 Synonyms

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
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Related Compounds: More...
SINAPIC ACID
622-31-1
cis-sinapic acid
7361-90-2
acetyl sinapic acid
90985-68-5
sinapic acid ethyl ester
69113-98-0
sinapic acid methyl ester
20733-94-2
sinapic acid choline ester
18696-26-9
Sinapic Acid Acyl-β-D-glucoside
14364-09-1
β-D-glucose ester of sinapic acid
78185-48-5
4-geranyl sinapic acid methyl ester
439944-28-2
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