13677-79-7

Basic information

• Product Name: 3,4,5-Trihydroxybenzaldehyde
• Synonyms: GALLALDEHYDE;3,4,5-TRIHYDROXYBENZALDHYDE;3,4,5-TRIHYDROXYBENZALDEHYDE;3,4,5-TRIHYDROXYBENZALDEHYDE HYDRATE 97%;3,4,5-TRIHYDROXYBNEZALDEHYDE MONOHYDRATE;3,4,5-Trihydroxybenzaldehyde hydrate, 97%, dry wt. basis;3,4,5-Trihydroxybenz;Pyrogallol-5-carboxaldehyde
• CAS NO: 13677-79-7
• Molecular Formula: C₇H₆O₄
• Molecular Weight: 154.12
• EINECS: 237-168-1
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aromatics;Inhibitors
• Mol File: 13677-79-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 211-213°C
• Boiling Point: 237.46°C (rough estimate)
• Flash Point: 182.9 °C
• Appearance: colorless and transparent liquid
• Density: 1.3725 (rough estimate)
• Vapor Pressure: 1.54E-05mmHg at 25°C
• Refractive Index: 1.6400 (estimate)
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: Soluble in DMSO and Methanol.
• PKA: 7.46±0.23(Predicted)
• Sensitive: Air Sensitive
• BRN: 2091654
• CAS DataBase Reference: 3,4,5-Trihydroxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5-Trihydroxybenzaldehyde(13677-79-7)
• EPA Substance Registry System: 3,4,5-Trihydroxybenzaldehyde(13677-79-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-36/37/39-37
• Hazardous Substances Data: 13677-79-7(Hazardous Substances Data)

Usage

Chemical Properties

Tan Solid

Uses

Different sources of media describe the Uses of 13677-79-7 differently. You can refer to the following data:
1. 3,4,5-trihydroxybenzaldehyde from Geum japonicum has dual inhibitory effect on matrix metalloproteinase 9; inhibition of gelatinoytic activity as well as MMP-9 expression in TNF-α induced HASMC.
2. THBA

InChI:InChI=1/C7H6O4/c8-3-4-1-5(9)7(11)6(10)2-4/h1-3,9-11H

Upstream product

• 134-96-3 syringic aldehyde 
• 6635-24-1 3,4,5-triacetoxybenzoic acid 
• 70475-59-1 3,4,5-triacetoxybenzoyl chloride 
• 1916-07-0 3,4,5-trimethoxybenzoic acid methyl ester 
• 3840-31-1 (3,4,5-trimethoxyphenyl)methanol 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 71932-18-8 3,4,5-tri-O-acetylbenzaldehyde 

Downstream Products

• 866122-72-7 3,4,5-tris-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-benzaldehyde 
• 6137-86-6 3,4,5-tribenzyloxybenzaldehyde 
• 752253-70-6 3,4,5-tris(tetradecyloxy)benzaldehyde 
• 126624-43-9 3,4,5-tris(methoxymethoxy)benzaldehyde 
• 1050432-42-2 C₁₄H₁₈N₂O₆ 
• 210890-95-2 8-hydroxy-2-[2-[(3,4,5-trihydroxyphenyl)ethenyl]]7-quinoline Carboxylic Acid 
• 757240-41-8 3,4,5-tris(3,7-dimethyloctyloxy)benzaldehyde 

Relevant articles and documents

Acid response water-soluble near-infrared BODIPY light-sensitive agent and preparation method thereof

The invention relates to an acid response water-soluble near-infrared BODIPY light-sensitive agent and a preparation method thereof. The novel BODIPY light-sensitive agent is soluble in water, has absorption performance in a near-infrared area, and has the advantages of being good in water solubility and high in light absorption in the near-infrared area. Meanwhile, the invention further provides the preparation method of the BODIPY light-sensitive agent. Synthesis is quick, and purification is easy. According to the preparation method, by reasonably designing feeding equivalence ratio, the target product can be obtained only through extraction, washing and other simple processing in triglycol monomethyl ether and p-toluenesulfonic acid sulfonylation; by means of the ethyl alcohol re-crystallization method, high-purity BODIPY is obtained; target molecules are synthesized at a high yield through reasonable temperature control. The method has the advantages of being easy to operate, convenient and safe to use and the like. The prepared light-sensitive agent can be soluble in water, the maximum absorption peak is 655 nm, the maximum emission peak is 710 nm, and the light emitting intensity of the light-sensitive agent is gradually improved along with addition of trifluoroacetic acid.

Bisdemethylcurcumin and structurally related hispolon analogues of curcumin exhibit enhanced prooxidant, anti-proliferative and anti-inflammatory activities in vitro

Curcumin, a component of turmeric (Curcuma longa), exhibits anti-inflammatory and anti-proliferative activities through the generation of reactive oxygen species (ROS). Curcumin (diferuloylmethane) contains two hydroxyl, two methoxy and two phenyl groups but how these groups contribute to its activity is poorly understood. We synthesized analogues that varied in inclusion of these groups and compared their activity. We found that bisdemethylcurcumin (BDC) was more potent than curcumin as an anti-inflammatory agent as indicated by suppression of TNF-induced NF-κB activation, more potent as an anti-proliferative agent, and more potent in inducing ROS. Hispolon, which lacks one aromatic unit in relation to curcumin, also exhibited enhanced anti-inflammatory and anti-proliferative activities. When synthetic curcumin (Cur-S) was compared with bisdemethylcurcumin (BDC), hispolon, hispolon methyl ether (HME), dehydroxy hispolon (DH), hydroxy hispolon (HH), methoxy hispolon methyl ether (MHME), and methoxy hispolon (MH), we found that following order of anti-inflammatory activity: BDC=Hispolon>HME>HH>Cur-S>MHME>MH>DH; for anti-proliferative: Hispolon>BDC>MHME>Cur-S>MH>HME=HH>DH; and for prooxidant: BDC>Cur-S=MHME>HH>MH+HME>DH (254-1414 mean fluorescence intensity). Thus, dehydroxy hispolon was least potent for all three activities. Overall the results indicate that the substitution of a hydroxyl group for a methoxy group at the meta positions of the phenyl rings in curcumin significantly enhanced the anti-inflammatory activity, and the removal of phenyl ring at the 7th position of the heptadiene back bone and addition of hydroxyl group significantly increased the anti-proliferative activity of curcumin.