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H36001

Sigma-Aldrich

Vanillic acid

97%

Synonym(s):

4-Hydroxy-3-methoxybenzoic acid

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About This Item

Linear Formula:
HOC6H3(OCH3)CO2H
CAS Number:
121-34-6
Molecular Weight:
168.15
Beilstein:
2208364
EC Number:
204-466-8
MDL number:
MFCD00002551
UNSPSC Code:
12352100
PubChem Substance ID:
24895581
NACRES:
NA.22
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Assay

97%

mp

208-210 °C (lit.)

SMILES string

COc1cc(ccc1O)C(O)=O

InChI

1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)

InChI key

WKOLLVMJNQIZCI-UHFFFAOYSA-N

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General description

Vanillic acid, also known as 4-Hydroxy-3-methoxybenzoic acid, is a phenolic molecule, commonly used as a building block in the synthesis of surfactants, flavorants, odorants, and plasticizers. [1] [2]

Application

  • Vanillin Synthesis from Vanillic Acid: Research focused on engineering the activity and thermostability of a carboxylic acid reductase for converting vanillic acid to vanillin, providing insights into biotechnological applications for flavor and fragrance industries (Ren et al., 2024).
  • Antioxidant Properties in Food Preservation: The antioxidant properties of vanillic acid were evaluated in a study on the preservation of postharvest quality and physicochemical properties of broccoli, suggesting its potential in extending the shelf life and nutritional quality of fresh produce (Kibar et al., 2024).
  • Biological Synthesis of Vanillin: A comprehensive review discussed various biological methods for synthesizing vanillin from vanillic acid, emphasizing its application in enhancing natural flavor profiles in the food sector (Venkataraman et al., 2024).
Vanillic acid is used as a starting material in the synthesis of:
  • aliphatic-aromatic polymers with good thermal stability and degradability [3]
  • novel polyesters via esterification and etherification reaction [4]

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBL4557
STBL3559
STBL0327
STBL2253
STBL1868

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Base metal iron catalyzed sustainable oxidation of vanillyl alcohol to vanillic acid in deep eutectic solvents and implementation of vanillic acid for fine-chemical synthesis
Rahul G, et al.
RSC Sustainability, 1, 1223-1232 (2023)
From Biomass to Bio-Based Polymers: Exploitation of Vanillic Acid for the Design of New Copolymers with Tunable Properties
Micaela V, et al.
Macromolecular Chemistry and Physics, 224, 2300001-2300001 (2023)
An overview of therapeutic effects of vanillic acid
Neha S, et al.
Plant Archives, 20, 3053-3059 (2020)
Synthesis and characterization of renewable polyesters based on vanillic acid
Silong Z, et al.
Journal of Applied Polymer Science, 137, 49189-49189 (2020)
Delphine Lamoral-Theys et al.
Bioorganic & medicinal chemistry, 18(11), 3823-3833 (2010-05-15)
A series of 33 novel divanillates and trivanillates were synthesized and found to possess promising cytostatic rather than cytotoxic properties. Several compounds under study decreased by >50% the activity of Aurora A, B, and C, and WEE1 kinase activity at
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Protocols

HPLC Analysis of Flavonoids on Ascentis® RP-Amide

Protocol for HPLC Analysis of Flavonoids on Ascentis® RP-Amide

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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