22014-01-3

Basic information

• Product Name: 3,5-DI-TERT-BUTYL-4-HYDROXYCINNAMIC ACID
• Synonyms: AKOS B004234;3,5-DI-TERT-BUTYL-4-HYDROXYCINNAMIC ACID;3,5-DI-T-BUTYL-4-HYDROXYCINNAMIC ACID;RARECHEM AL BK 0198;TIMTEC-BB SBB001103;3,5-Di-tert-butyl-4-hydroxycinnamic acid, predominantly trans, 98%;Nsc 226266;3-(3,5-Di-tert-butyl-4-hydroxyphenyl)acrylic acid
• CAS NO: 22014-01-3
• Molecular Formula: C₁₇H₂₄O₃
• Molecular Weight: 276.37
• EINECS: -0
• Product Categories: Aromatic Cinnamic Acids, Esters and Derivatives
• Mol File: 22014-01-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 193-196°C
• Boiling Point: 375℃
• Flash Point: 195℃
• Appearance: /
• Density: 1.076
• Vapor Pressure: 2.66E-06mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.71±0.10(Predicted)
• Water Solubility: Soluble in water.
• BRN: 3144594
• CAS DataBase Reference: 3,5-DI-TERT-BUTYL-4-HYDROXYCINNAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DI-TERT-BUTYL-4-HYDROXYCINNAMIC ACID(22014-01-3)
• EPA Substance Registry System: 3,5-DI-TERT-BUTYL-4-HYDROXYCINNAMIC ACID(22014-01-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-37
• Hazardous Substances Data: 22014-01-3(Hazardous Substances Data)

Usage

Uses

3,5-Di-tert-butyl-4-hydroxycinnamic acid, predominantly trans,

InChI:InChI=1/C17H24O3/c1-16(2,3)12-9-11(7-8-14(18)19)10-13(15(12)20)17(4,5)6/h7-10,20H,1-6H3,(H,18,19)/p-1/b8-7+

Upstream product

• 64-19-7 acetic acid 
• 1620-98-0 3,5-di-t-butyl-4-hydroxybenzaldehyde 
• 99591-64-7 3-(1-Amino-3,5-di-tert-butyl-4-oxo-cyclohexa-2,5-dienyl)-propionic acid 
• 108-24-7 acetic anhydride 
• 141-82-2 malonic acid 

Downstream Products

• 595558-98-8 6-amino-5-(3,5-di-tert-butyl-4-hydroxycinnamoylamido)-3-methyl-1-phenyl-2,4-(1H,3H)-pyrimidinedione 
• 809-73-4 3,3',5,5'-tetra-tert-butyl-4,4'-stilbenequinone 
• 42153-98-0 4,4'-(2-butene-1,4-diylidene)-bis(2,6-di-tert-butyl-2,5-cyclohexadien-1-one) 
• 1284260-30-5 C₃₄H₄₄Cl₂N₂O₅ 
• 97086-32-3 1.4-Bis-<4-hydroxy-3.5-di-tert.-butyl-phenyl>-butan-dicarbonsaeure-dimethylester-(2.3) 
• 65849-89-0 dimethyl 2,3-bis[[3,5-bis(tert-butyl)-4-oxo-2,5-cyclohexadien-1-ylidene]methyl]butanedionate 
• 103772-79-8 (Z)-3-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-1-piperidin-1-yl-propenone 
• 103772-78-7 (Z)-N-Butyl-3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-acrylamide 
• 35186-94-8 4-Hydroxy-3,5-di-tert-butyl-zimtsaeure-aethylester 
• 111721-69-8 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-(diphenylphosphinyl)-propionohydrazide 
• 865087-47-4 2,6-di-tert-butyl-4-{2-[4-(3,5-dimethyl-pyridin-4-yl)-3,5-dimethyl-phenyl]-vinyl}phenol 
• 19263-36-6 2,6-di-tert-butyl-4-vinyl-phenol 
• 134503-13-2 (Z)-3-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-acryloyl chloride 
• 27574-90-9 methyl β-(3,5-di-tert-butyl-4-hydroxyphenyl)acrylate 

Relevant articles and documents

Isolation, identification, and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis

The tumor microenvironment is characterized by hypoxia, low-nutrient levels, and acidosis. A natural product chemistry-based approach was used to discover small molecules that modulate adaptive responses to a hypoxic microenvironment through the hypoxia-inducible factor (HIF)-1 signaling pathways. Five compounds, such as baccharin (3), beturetol (4), kaempferide (5), isosakuranetin (6), and drupanin (9), that modulate HIF-1-dependent luciferase activity were identified from Brazilian green propolis using reporter assay. Compounds 3, 9 and 5 reduced HIF-1-dependent luciferase activity. The cinnamic acid derivatives 3 and 9 significantly inhibited expression of the HIF-1α protein and HIF-1 downstream target genes such as glucose transporter 1, hexokinase 2, and vascular endothelial growth factor A. They also exhibited significant anti-angiogenic effects in the chick chorioallantoic membrane (CAM) assay at doses of 300 ng/CAM. On the other hand, flavonoids 4 and 6 induced HIF-1-dependent luciferase activity and expression of HIF-1 target genes under hypoxia. The contents (g/100 g extract) of the HIF-1-modulating compounds in whole propolis ethanol extracts were also determined based on liquid chromatography-electrospray ionization mass spectrometry as 1.6 (3), 14.2 (4), 4.0 (5), 0.7 (6), and 0.7 (9), respectively. These small molecules screened from Brazilian green propolis may be useful as lead compounds for the development of novel therapies against ischemic cardiovascular disease and cancer based on their ability to induce or inhibit HIF-1 activity, respectively.

Studies on styrene derivatives. II. Synthesis and antiinflammatory activity of 3,5-di-tert-butyl-4-hydroxystyrenes

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