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Vanillic acid

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Identification
Molecular formula
C8H8O4
CAS number
121-34-6
IUPAC name
4-hydroxy-3-methoxy-benzoic acid
State
State

Vanillic acid is typically found as a solid at room temperature. It is relatively stable under standard conditions and has low solubility in water, making it a convenient compound for various solid-state applications.

Melting point (Celsius)
210.00
Melting point (Kelvin)
483.15
Boiling point (Celsius)
440.00
Boiling point (Kelvin)
713.15
General information
Molecular weight
168.15g/mol
Molar mass
168.1510g/mol
Density
1.3580g/cm3
Appearence

Vanillic acid appears as white or slightly yellow crystalline needles. It is often found as a powder used in various applications, especially in flavor and fragrance industries. It emits a faint sweet aroma reminiscent of vanilla.

Comment on solubility

Solubility of 4-hydroxy-3-methoxy-benzoic acid

4-hydroxy-3-methoxy-benzoic acid, commonly known as vanillic acid, exhibits some intriguing solubility characteristics that are worth exploring.

This compound demonstrates solubility in various solvents, particularly:

  • Water: Vanillic acid is moderately soluble in water, which can be attributed to the presence of its hydroxyl (-OH) groups that can form hydrogen bonds with water molecules.
  • Organic Solvents: It is more soluble in organic solvents like ethanol and methanol. The aromatic structure allows for interaction with non-polar parts of these solvents.

Additionally, the solubility can be influenced by factors such as:

  • Temperature: Increased temperature often enhances solubility, making vanillic acid more soluble in hot water compared to its solubility at room temperature.
  • pH: The acid dissociation can vary with pH. In higher pH environments, the carboxylic acid group can lose a proton, leading to increased solubility due to the formation of anionic species.

In summary, vanillic acid's solubility is multifaceted and is governed by its chemical structure and external conditions. As noted, the compound is more soluble in organic solvents and shows moderate solubility in aqueous solutions, making it versatile for various applications. Understanding these solubility properties can facilitate its use in different chemical and biological contexts.

Interesting facts

Interesting Facts About 4-Hydroxy-3-methoxy-benzoic Acid

4-Hydroxy-3-methoxy-benzoic acid, commonly known as vanillic acid, is a fascinating compound with diverse applications and properties that pique the interest of many in the field of chemistry.

Chemical Structure and Properties

This compound is characterized by:

  • A hydroxyl group (-OH) which contributes to its acidity and solubility in water.
  • A methoxy group (-OCH3) that enhances its flavor and aromatic profile.
  • An aromatic benzoic acid structure that is pivotal in numerous biological and chemical reactions.

Natural Occurrence

Vanillic acid occurs naturally in various sources, making it a significant compound in nature:

  • Found in vanilla beans, it imparts a sweet, pleasant flavor.
  • Present in certain fruits and vegetables, contributing to their unique aromatic profiles.

Applications

Its multifunctional nature has led to various applications:

  • Used as a flavoring agent in the food industry due to its vanilla-like taste.
  • Utilized in cosmetic formulations for its antioxidant properties.
  • Serves as a precursor in the synthesis of various pharmaceuticals and bioactive compounds.

Biological Significance

Research indicates that vanillic acid may possess several health benefits:

  • Antioxidant Activity: It can help neutralize free radicals, reducing oxidative stress.
  • Anti-inflammatory Properties: Studies suggest it may reduce inflammation in various biological systems.
  • Potential Antimicrobial Effects: There is ongoing investigation into its ability to combat certain pathogens.

In conclusion, the study of 4-hydroxy-3-methoxy-benzoic acid not only reveals its structural intricacies but also its broad implications in both culinary and health-related fields, making it a compound of significant interest for ongoing research and applications.

Synonyms
Vanillic acid
4-HYDROXY-3-METHOXYBENZOIC ACID
121-34-6
Acide vanillique
p-Vanillic acid
Benzoic acid, 4-hydroxy-3-methoxy-
3-Methoxy-4-hydroxybenzoic acid
m-Anisic acid, 4-hydroxy-
Vanillate
VanillicAcid
Protocatechuic acid, 3-methyl ester
NSC 3987
MFCD00002551
NSC 674322
4-hydroxy-3-methoxy-Benzoic acid
UNII-GM8Q3JM2Y8
4-Hydroxy-3-methoxybenzoate
EINECS 204-466-8
GM8Q3JM2Y8
BRN 2208364
CHEBI:30816
AI3-19542
NSC-3987
NSC-674322
VA
CHEMBL120568
DTXSID6059522
FEMA NO. 3988
DROXIDOPA METABOLITE (VA)
4-hydroxy-3-methoxy benzoic acid
2-METHOXY-4-CARBOXYPHENOL
NSC674322
M-METHOXY-P-HYDROXY-BENZOIC ACID
Acid, Vanillic
VA (VAN)
VNL
4-hydroxy-m-Anisic acid
Vanillinsaure
p-Vanillate
Vanilic acid
4-Hydroxy-3-methoxybenzoicacid
4 Hydroxy 3 methoxybenzoic Acid
p Hydroxy m methoxy benzoic Acid
p-Hydroxy-m-methoxy-benzoic Acid
Acid, 4-Hydroxy-3-methoxybenzoic
Acid, p-Hydroxy-m-methoxy-benzoic
4-hydroxy-m-Anisate
Vanillic acid (M2)
Vanillic acid, 97%
Vanillic acid (Standard)
bmse000486
bmse000614
bmse010205
WLN: QVR DQ CO1
VANILLIC ACID [MI]
3-Methoxy-4-hydroxybenzoate
SCHEMBL26179
MLS000574833
4-hydroxy-3-methoxy-Benzoate
Vanillic acid, >=97%, FG
4-hydroxy-3methoxy benzoic acid
DTXCID1033668
HY-N0708R
4-hydroxyl-3-methoxybenzoic acid
NSC3987
4- hydroxy-3-methoxybenzoic acid
HMS2197E16
Protocatechuic acid 3-methyl ester
HY-N0708
STR02334
BBL011982
BDBM50337364
CK2172
s5343
STL163472
AKOS000113195
CCG-266343
FH00443
NCGC00247610-01
1ST40128
AC-11841
BP-13246
SMR000156289
SY001450
DB-003804
Vanillic acid, purum, >=97.0% (HPLC)
CS-0009728
NS00014581
V0017
4-HYDROXY-3-METHOXYBENZOIC ACID [FHFI]
C06672
EN300-105765
Vanillic acid, Vetec(TM) reagent grade, 97%
AM-331/20714013
Q419672
Z381356666
Vanillic acid, certified reference material, TraceCERT(R)
3E9555E5-85F5-4FCE-A429-5182E959C6A3
InChI=1/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11
204-466-8