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E24859

Sigma-Aldrich

Protocatechuic acid ethyl ester

97%

Synonym(s):

Ethyl 3,4-dihydroxybenzoate

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About This Item

Linear Formula:
(HO)2C6H3CO2C2H5
CAS Number:
3943-89-3
Molecular Weight:
182.17
EC Number:
223-529-0
MDL number:
MFCD00002199
UNSPSC Code:
12352100
PubChem Substance ID:
24894472
NACRES:
NA.22

Quality Level

100

Assay

97%

mp

132-134 °C (lit.)

SMILES string

CCOC(=O)c1ccc(O)c(O)c1

InChI

1S/C9H10O4/c1-2-13-9(12)6-3-4-7(10)8(11)5-6/h3-5,10-11H,2H2,1H3

InChI key

KBPUBCVJHFXPOC-UHFFFAOYSA-N

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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S A Fisher et al.
Journal of molecular and cellular cardiology, 26(6), 721-731 (1994-06-01)
The extra-cellular matrix has been demonstrated to play an important role in the differentiation of a number of cell types in vitro. The purpose of this study was to establish the role of ECM collagen synthesis in regulating growth and
Sebastian Philipp et al.
American journal of physiology. Heart and circulatory physiology, 290(1), H450-H457 (2005-09-13)
Protection from a prolyl hydroxylase domain-containing enzyme (PHD) inhibitor, desferoxamine (DFO), was recently reported to be dependent on production of reactive oxygen species (ROS). Ischemic preconditioning triggers the protected state by stimulating nitric oxide (NO) production to open mitochondrial ATP-sensitive
Jian Wang et al.
FEBS letters, 529(2-3), 309-312 (2002-10-10)
Ethyl-3,4-dihydroxybenzoate (EDHB) is commonly utilized as a substrate analog and competitive inhibitor of prolyl 4-hydroxylases. These iron-dependent enzymes have received a lot of attention for their involvement in crucial biochemical pathways such as collagen maturation and oxygen sensing. Since EDHB
Tanveer Ahmad et al.
American journal of respiratory cell and molecular biology, 47(1), 1-10 (2012-02-09)
Oxygen-sensing prolyl-hydroxylase (PHD)-2 negatively regulates hypoxia-inducible factor (HIF)1-α and suppresses the hypoxic response. Hypoxia signaling is thought to be proinflammatory but also attenuates cellular injury and apoptosis. Although increased hypoxic response has been noted in asthma, its functional relevance is
Christina Warnecke et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 17(9), 1186-1188 (2003-04-24)
Hypoxia-inducible transcription factors (HIF) mediate complex adaptations to reduced oxygen supply, including neoangiogenesis. Regulation of HIF occurs mainly through oxygen-dependent destruction of its alpha subunit. In the presence of oxygen, two HIFalpha prolyl residues undergo enzymatic hydroxylation, which is required
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