Ethyl 3,4-dihydroxybenzoate

Modify Date: 2024-01-02 20:06:16

Ethyl 3,4-dihydroxybenzoate Structure
Ethyl 3,4-dihydroxybenzoate structure
 Common Name Ethyl 3,4-dihydroxybenzoate
CAS Number 3943-89-3 Molecular Weight 182.173
Density 1.3±0.1 g/cm3 Boiling Point 358.1±22.0 °C at 760 mmHg
Molecular Formula C9H10O4 Melting Point 132-134 °C(lit.)
MSDS Chinese USA Flash Point 147.0±15.8 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Ethyl 3,4-dihydroxybenzoate


Ethyl 3,4-dihydroxybenzoate (Ethyl protocatechuate), an antioxidant, is a prolyl-hydroxylase inhibitor found in the testa of peanut seeds. Ethyl 3,4-dihydroxybenzoate protects myocardium by activating NO synthase and generating mitochondrial ROS. Ethyl 3,4-dihydroxybenzoate induces cell autophagy and apoptosis in ESCC cells. Ethyl 3,4-dihydroxybenzoate is a collagen synthesis inhibitor and has a bone protecting-effect[1][2][3][4].

 Names

Name Ethyl 3,4-dihydroxybenzoate
Synonym More Synonyms

 Ethyl 3,4-dihydroxybenzoate Biological Activity

Description Ethyl 3,4-dihydroxybenzoate (Ethyl protocatechuate), an antioxidant, is a prolyl-hydroxylase inhibitor found in the testa of peanut seeds. Ethyl 3,4-dihydroxybenzoate protects myocardium by activating NO synthase and generating mitochondrial ROS. Ethyl 3,4-dihydroxybenzoate induces cell autophagy and apoptosis in ESCC cells. Ethyl 3,4-dihydroxybenzoate is a collagen synthesis inhibitor and has a bone protecting-effect[1][2][3][4].
Related Catalog
References

[1]. Bo Han, et al. A prolyl-hydroxylase inhibitor, ethyl-3,4-dihydroxybenzoate, induces cell autophagy and apoptosis in esophageal squamous cell carcinoma cells via up-regulation of BNIP3 and N-myc downstream-regulated gene-1. PLoS One. 2014 Sep 18;9(9):e107204.

[2]. Sebastian Philipp, et al. Desferoxamine and ethyl-3,4-dihydroxybenzoate protect myocardium by activating NOS and generating mitochondrial ROS. Am J Physiol Heart Circ Physiol. 2006 Jan;290(1):H450-7.

[3]. Byeong-Ju Kwon, et al. Ethyl-3,4-dihydroxybenzoate with a dual function of induction of osteogenic differentiation and inhibition of osteoclast differentiation for bone tissue engineering. Tissue Eng Part A. 2014 Nov;20(21-22):2975-84.

[4]. D Nandan, et al. Ethyl-3,4-dihydroxybenzoate inhibits myoblast differentiation: evidence for an essential role of collagen. J Cell Biol. 1990 May;110(5):1673-9.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 358.1±22.0 °C at 760 mmHg
Melting Point 132-134 °C(lit.)
Molecular Formula C9H10O4
Molecular Weight 182.173
Flash Point 147.0±15.8 °C
Exact Mass 182.057907
PSA 66.76000
LogP 2.22
Vapour Pressure 0.0±0.8 mmHg at 25°C
Index of Refraction 1.574

 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 2918290000

 Synthetic Route

protocatechuic acid structure

protocatechuic acid

CAS#:99-50-3

Ethanol structure

Ethanol

CAS#:64-17-5

~99%

Ethyl 3,4-dihydroxybenzoate Structure

Ethyl 3,4-dihyd...

CAS#:3943-89-3

Literature: Rey, Jimena; Garcia, Felix Clemente; Garcia, Jose Miguel Reactive and Functional Polymers, 2011 , vol. 71, # 9 p. 948 - 957
ethyl 4-((di-tert-butyl(hydroxy)silyl)oxy)benzoate structure

ethyl 4-((di-te...

CAS#:1344113-41-2

~78%

Ethyl 3,4-dihydroxybenzoate Structure

Ethyl 3,4-dihyd...

CAS#:3943-89-3

Literature: Huang, Chunhui; Ghavtadze, Nugzar; Chattopadhyay, Buddhadeb; Gevorgyan, Vladimir Journal of the American Chemical Society, 2011 , vol. 133, # 44 p. 17630 - 17633
Ethyl 3,4-dihydro-2H-benzo[b][1,4]dioxepine-7-carboxylate structure

Ethyl 3,4-dihyd...

CAS#:20986-39-4

~90%

Ethyl 3,4-dihydroxybenzoate Structure

Ethyl 3,4-dihyd...

CAS#:3943-89-3

Literature: Huang, Wei-Bin; Guo, Ying; Jiang, Jian-An; Pan, Xian-Dao; Liao, Dao-Hua; Ji, Ya-Fei Synlett, 2013 , vol. 24, # 6 art. no. ST-2013-W0052-L, p. 741 - 746
Ethylparaben structure

Ethylparaben

CAS#:120-47-8

~%

Ethyl 3,4-dihydroxybenzoate Structure

Ethyl 3,4-dihyd...

CAS#:3943-89-3

Literature: Huang, Chunhui; Ghavtadze, Nugzar; Chattopadhyay, Buddhadeb; Gevorgyan, Vladimir Journal of the American Chemical Society, 2011 , vol. 133, # 44 p. 17630 - 17633
Hydrochloric acid structure

Hydrochloric acid

CAS#:7647-01-0

protocatechuic acid structure

protocatechuic acid

CAS#:99-50-3

Ethanol structure

Ethanol

CAS#:64-17-5

~%

Ethyl 3,4-dihydroxybenzoate Structure

Ethyl 3,4-dihyd...

CAS#:3943-89-3

Literature: Matsmoto Chemische Berichte, 1878 , vol. 11, p. 133

 Customs

HS Code 2918290000
Summary HS: 2918290000 other carboxylic acids with phenol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) VAT:17.0% MFN tariff:6.5% General tariff:30.0%

 Articles30

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Antioxidant activity of protocatechuates evaluated by DPPH, ORAC, and CAT methods.

Food Chem. 194 , 749-57, (2015)

Hibiscus sabdariffa L. is a worldwide consumed plant, principally after infusion of its dried sepals and calyces, which are usually discarded. Nevertheless, they represent a potential source of natura...

Inhibitory Effect of Dried Pomegranate Concentration Powder on Melanogenesis in B16F10 Melanoma Cells; Involvement of p38 and PKA Signaling Pathways.

Int. J. Mol. Sci. 16 , 24219-42, (2015)

Plants rich in antioxidant substances may be useful for preventing skin aging. Pomegranates, containing flavonoids and other polyphenolic compounds, are widely consumed due to their beneficial propert...

Evidence for a role of collagen synthesis in arterial smooth muscle cell migration.

J. Clin. Invest. 101(9) , 1889-98, (1998)

Migration of smooth muscle cells (SMCs) and collagen synthesis by SMCs are central to the pathophysiology of vascular disease. Both processes can be induced shortly after vascular injury; however, a f...

 Synonyms

3,4-dihydroxybenzoic acid ethyl ether
Ethyl-3,4-dihydroxybenzoate
Benzoic acid, 3,4-dihydroxy-, ethyl ester
Ethyl protocatechuate
EDHB
3,4-Dihydroxybenzoic acid ethyl ester
EINECS 223-529-0
Benzoic acid, 3,4-dihydroxy-, ethyl ester (9CI)
Protocatechuic acid ethyl ester
MFCD00002199
Ethyl 3,4-dihydroxybenzoate
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