Vanillin

US Previously Marketed

First marketed in 1921

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H8O3
Molecular Weight	152.1473
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(C=O)=CC=C1O

InChI

InChIKey=MWOOGOJBHIARFG-UHFFFAOYSA-N

InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3

HIDE SMILES / InChI

Molecular Formula	C8H8O3
Molecular Weight	152.1473
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27038927 | https://www.ncbi.nlm.nih.gov/pubmed/28077989 | https://www.ncbi.nlm.nih.gov/pubmed/27084583

Vanillin (4-hydroxy-3-methoxybenzaldehyde), a pleasant smelling organic aromatic compound, is widely used as a flavoring additive in food, beverage, cosmetic and drug industries. It is reported to cross the blood brain barrier and also displayed antioxidant and neuroprotective activities. Vanillin is a natural substance widely found in many plant species and often used in beverages, foods, cosmetics, and pharmaceutical products. Antioxidant and anticancer potential have been described for this compound. Vanillin has been classified as a bioantimutagen and is able to inhibit mutagenesis induced by chemical and physical mutagens in various cell systems. Vanillin, a selective agonist of TRPV1, has been shown to attenuate i.c.v. STZ and AlCl3+d-galactose induced experimental Alzheime's disease (AD).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Oxidative Stress 162 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28077989	Inhibitor 8504	16.25 µM [IC50]
Alpha-glucosidase MAL62 4 Target ID: CHEMBL4357 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25674660	Inhibitor 8504	81.5 µM [IC50]
Acetylcholinesterase 209 Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23715789	Inhibitor 8504	0.037 mM [IC50]
Transient receptor potential cation channel subfamily V member 1 6 Target ID: CHEMBL1781864 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27084583	Agonist 2752

Conditions

Condition	Modality	Highest Phase	Product
Parkinson's disease 232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27038927	Primary	Preclinical	Unknown Approved Use Unknown
Premature newborns 1 Sources: https://clinicaltrials.gov/ct2/show/NCT02630147	Palliative	Phase I 438	Unknown Approved Use Unknown
Toxoplasmosis 13 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24810805	Primary	Preclinical	Unknown Approved Use Unknown
Alzheimer’s disease 278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23715789	Primary	Preclinical	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741 CYP2E1 1060 CYP2B6 926 CYP1A2 2153	UGT1A1 479 UGT1A3 470 UGT1A4 399 UGT1A6 343 UGT1A7 249 UGT1A8 323 UGT1A9 423 UGT1A10 331 UGT2B4 278 UGT2B7 456 UGT2B15 236 UGT2B17 237

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22450566/	no
CYP2B6 1160	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22450566/	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22450566/	no
CYP2E1 1146	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22450566/	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22450566/	no
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/29502118/	yes
P-gp 1932	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/29502118/	yes

Drug as victim

Target	Modality	Activity
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23184728/	no
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23184728/	no
UGT2B4 278	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23184728/	no
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23184728/	yes
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23184728/	yes
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23184728/	yes
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23184728/	yes
UGT1A7 249	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23184728/	yes
UGT1A8 323	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23184728/	yes
UGT2B15 236	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23184728/	yes
UGT2B17 237	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23184728/	yes
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23184728/	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	NO13553	https://www.001chemical.com/chem/121-33-5
3B Scientific (Wuhan) Corp	3B3-020392	http://www.3bsc.com/index/pro_info.php?id=29361
AA Blocks	AA0037UC	http://www.aablocks.com/goods/Goods/detail?id=AA0037UC
Aaron Chemicals	AR0038M4	http://www.aaronchem.com/121-33-5
abcr GmbH	AB117415	http://www.abcr.com/shop/en/AB117415
Acadechem	ACDS-017525	http://www.acadechemical.com/product/92224
Accela ChemBio Inc	SY224451	http://www.accelachem.com/cn/search.html?keyword=SY224451&attname=GoodsCode
Aceschem	ACS014278	https://www.aceschem.com/catalog/121-33-5.html
Achemica	ACMC-1BURM	http://www.achemica.com/prodinfo/?id=70173
Achemo Scientific Limited	AC-62290	http://www.achemo.com/search/?Keyword= 121-33-5
Achemtek	0104-011520	http://www.achemtek.com/121-33-5
Acorn PharmaTech	ACN-046875	http://www.acornpharmatech.com/
Acros Organics	AC140820020	https://www.fishersci.com/shop/products/vanillin-99-pure-acros-organics/AC140820020
Acros Organics	AC140820050	https://www.fishersci.com/shop/products/vanillin-99-pure-acros-organics-4/AC140820050
Acros Organics	AC140822500	https://www.fishersci.com/shop/products/vanillin-99-pure-acros-organics/AC140822500
AHH Chemical co.,ltd	MT-15168	http://www.ahhchemical.com/product/MT-15168.html
AHH Chemical co.,ltd	NP-0916	http://www.ahhchemical.com/product/NP-0916.html
AK Scientific, Inc. (AKSCI)	71554	http://www.aksci.com/item_detail.php?cat=71554
Alfa Aesar	A11169	https://www.alfa.com/en/catalog/A11169/
Alfa Chemistry	AP121335	https://reagents.alfa-chemistry.com/product/vanillin-cas-121-33-5-2789.html
Alfa Chemistry	AP121335-A	https://reagents.alfa-chemistry.com/product/mettler-toledo-calibration-substance-me-cas-121-33-5-2790.html
Alfa Chemistry	AP121335-B	https://reagents.alfa-chemistry.com/product/vanillin-melting-point-standard-cas-121-33-5-2791.html
Alfa Chemistry	AP121335-C	https://reagents.alfa-chemistry.com/product/vanillin-cas-121-33-5-2792.html
Ambinter	Amb1880873	http://www.ambinter.com/reference/1880873
Angene	AGN-PC-0084T7	http://www.angenechemical.com/productshow/AGN-PC-0084T7.html
Anward	ANW-17588	http://www.anward.com/pro_result/30307
ApexBio Technology	B3679	http://www.apexbt.com/vanillin.html
Ark Pharm	AK-32997	http://www.arkpharminc.com/products/121-33-5.html
Aurora Fine Chemicals LLC	A00.156.184	http://online.aurorafinechemicals.com/info?ID=A00.156.184
Aurum Pharmatech LLC	MP-2189	http://www.Aurumpharmatech.com/Product/ProductDetails/MP_2189
Avantor Inc	101094-034	https://us.vwr.com/store/product/22573392/vanillin-melting-point-standard-usp
Avantor Inc	200021-144	https://us.vwr.com/store/product/7515200/vanillin
Avantor Inc	BT125060-100G	https://us.vwr.com/store/product/16636859/vanillin-99
Avantor Inc	BT125060-2.5KG	https://us.vwr.com/store/product/16636859/vanillin-99
Avantor Inc	BT125060-500G	https://us.vwr.com/store/product/16636859/vanillin-99
BenchChem	B546587	https://www.benchchem.com/product/b546587
BioChemPartner	BCP29943	http://www.biochempartner.com/121-33-5-BCP29943
BioCrick	BCN2605	http://www.biocrick.com/Vanillin-BCN2605.html
BioSynth	Q-100102	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-100102.html
BLD Pharm	BD01094730	http://www.bldpharm.com/products/121-33-5.html
BLD Pharm	BD17795	http://www.bldpharm.com/products/121-33-5.html
BOC Sciences	201595-58-6	https://www.bocsci.com/vanillin-13c6-cas-201595-58-6-item-264349.html
BOC Sciences	74495-74-2	https://www.bocsci.com/4-hydroxy-3-methoxybenzaldehyde-d3-cas-74495-74-2-item-241473.html
BOC Sciences	86884-84-6	https://isotope.bocsci.com/product/vanillin-methoxy-13c-cas-86884-84-6-344140.html
BroadPharm	BP-10602	http://www.broadpharm.com/web/product.php?catalog=BP-10602
Chem Scene	CS-W020052	http://www.chemscene.com/121-33-5.html
ChemFaces	CFN90463	http://www.chemfaces.com/natural/Vanillin-CFN90463.html
ChemMol	30100345	http://www.chemmol.com/chemmol/30100345.html
ChemMol	44009553	http://www.chemmol.com/chemmol/44009553.html
ChemMol	49415621	http://www.chemmol.com/chemmol/49415621.html
ChemMol	83600561	http://www.chemmol.com/chemmol/83600561.html
ChemShuttle	113559	http://www.chemshuttle.com/catalogsearch/result/?q=121-33-5&cat=
Chemspace	CSSB00000188322	https://chem-space.com/CSSB00000188322
China MainChem Co., Ltd	121-33-5	https://www.mainchem.com/product/china-vanillin-supplier-cas-121-33-5-distributor/
China MainChem Co., Ltd	MS121-33-5	https://www.mainchem.com/product/vanillin/
Clearsynth	CS-EB-02223	https://www.clearsynth.com/en/CSEB02223.html
Clearsynth	CS-ER-02226	https://www.clearsynth.com/en/CSER02226.html
Clearsynth	CS-O-11767	https://www.clearsynth.com/en/CSO11767.html
Clearsynth	CS-T-87651	https://www.clearsynth.com/en/CST87651.html
CSNpharm	CSN12510	https://www.csnpharm.com/products/vanillin.html
DC Chemicals	DCX-012	http://www.dcchemicals.com//product_show-Vanillin.html
Debye Scientific	DB-003805	http://www.debyesci.com/DB-003805.html
eNovation Chemicals	D541103	http://www.enovationchem.com/productDetails.asp?productID=D541103
eNovation Chemicals	D599973	https://www.enovationchem.com/ProductDetails.asp?ProductID=D599973
Finetech	FT-0618639	http://www.finetechnology-ind.com/prod/detail/pub/121-33-5.html
Finetech	FT-0669738	http://www.finetechnology-ind.com/prod/detail/pub/74495-74-2.html
Finetech	FT-0675778	http://www.finetechnology-ind.com/prod/detail/pub/201595-58-6.html
Fisher Chemical	V10100	https://www.fishersci.com/shop/products/vanillin-crystalline-nf-fisher-chemical/V10100
FondChemical	FDB-1367	http://www.fondchemical.com/cpshow_cid_8_pid_555.html
Glentham Life Sciences	GP6341	http://www.glentham.com/products/product/GP6341/
Hairui	CUSA07106	http://www.hairuichem.com/en/product/121-33-5.html
Huateng Pharma	F80004131	http://en.huatengsci.com/product/Vanillin.html
iChemical	EBD162138	http://www.ichemical.com/products/121-33-5.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00335569	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00335569
LGC Standards	DRE-C17900580	https://www.lgcstandards.com/US/en/p/DRE-C17900580
LGC Standards	MM1447.00-0250	https://www.lgcstandards.com/US/en/p/MM1447.00-0250
Matrix Scientific	133924	https://www.matrixscientific.com/133924.html
mcule	MCULE-1294709490	https://mcule.com/MCULE-1294709490/
MedChem Express	HY-N0098	https://www.medchemexpress.com/Vanillin.html
Molcore	CS13553	https://www.molcore.com/product/121-33-5
MuseChem	R050700	https://www.musechem.com/product/R050700.html
Oakwood	32468	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=26346&ExtHyperLink=1
Otava	109160039	https://search.otavachemicals.com/#!/search?query=0109160039&type=code&base=dbb
Parchem	33171	http://www.parchem.com/chemical-supplier-distributor/Nat-Vanillin-023171.aspx
Parchem	691	http://www.parchem.com/chemical-supplier-distributor/Vanillin-001456.aspx
R&D Chemicals	6110	http://www.rdchemicals.com/chemicals.php?mode=details&mol_id=8332
Renno Tech	RP21590	http://www.rennotech.com/product_show.asp?id=27306
Sigma-Aldrich	1710006_USP	https://www.sigmaaldrich.com/catalog/product/usp/1710006?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1711009_USP	https://www.sigmaaldrich.com/catalog/product/usp/1711009?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	30304_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/30304?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	33-0249_SAJ	https://www.sigmaaldrich.com/catalog/product/saj/330249?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	77634_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/77634?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S001868	http://www.sinfoobiotech.com/product/1005266
Smolecule	S546587	http://www.smolecule.com/products/s546587
TCI (Tokyo Chemical Industry)	H0264	http://www.tcichemicals.com/eshop/en/us/commodity/H0264/index.html
TCI (Tokyo Chemical Industry)	V0080	http://www.tcichemicals.com/eshop/en/us/commodity/V0080/index.html
THE BioTek	bt-285703	https://www.thebiotek.com/product/inhibitors/bt-285703
VladaChem	VL145036	https://www.vladachem.com/product.php?products=121-33-5
VladaChem	VL165789	https://www.vladachem.com/product.php?products=121-33-5
VladaChem	VL266212-500G	https://www.vladachem.com/product.php?products=121-33-5
Wuhan Atomole Chemicals Co., Ltd.	AT-15565	http://www.atomole.com/en/products-view.asp?id=5083
Yuhao Chemical	RT11342	http://www.chemyuhao.com/201595-58-6.html

PubMed

Title	Date	PubMed
Changes in low molecular weight phenolic compounds in Spanish, French, and American oak woods during natural seasoning and toasting.	2001 Apr	11308327
Human potency predictions for aldehydes using the local lymph node assay.	2001 Aug	11553118
Aroma-active components of nonfat dry milk.	2001 Jun	11409991
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.	2001 Mar	11258977
Antioxidant activity of resveratrol compared with common food additives.	2001 Mar	11252483
Changes in the phenolic composition of virgin olive oil from young trees (Olea europaea L. cv. Arbequina) grown under linear irrigation strategies.	2001 Nov	11714351
The coenzyme A-dependent, non-beta-oxidation pathway and not direct deacetylation is the major route for ferulic acid degradation in Delftia acidovorans.	2001 Nov 27	11728709
Free radical scavenging activity of vanillin and o-vanillin using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical.	2002	11981453
Conservation and diversity of gene families explored using the CODEHOP strategy in higher plants.	2002 Aug 1	12153706
Asymmetry of pleasant vs. unpleasant odor processing during affective judgment in humans.	2002 Aug 16	12147332
Chromone and phenanthrene alkaloids from Dennettia tripetala.	2002 Dec	12499602
Colorimetric and fluorimetric methods for determination of panthenol in cosmetic and pharmaceutical formulation.	2002 Feb 1	11814714
Volatile components of Loureira, Dona Branca, and Treixadura wines.	2002 Jan 30	11804526
A biotechnological process involving filamentous fungi to produce natural crystalline vanillin from maize bran.	2002 Jul-Dec	12396118
Determination of available phenolic compounds in soils by liquid chromatography with solid-phase extraction.	2002 Nov-Dec	12477182
Quantitation of odor-active compounds in rye flour and rye sourdough using stable isotope dilution assays.	2002 Sep 11	12207478
Changes in the HPLC phenolic profile of virgin olive oil from young trees (Olea europaea L. Cv. Arbequina) grown under different deficit irrigation strategies.	2002 Sep 11	12207473
A novel strategy for the synthesis of benzofuran skeleton neolignans: application to ailanthoidol, XH-14, and obovaten.	2002 Sep 20	12227810
Probing suggested catalytic domains of glycosyltransferases by site-directed mutagenesis.	2003 Feb	12542702
Colorimetric determination of gabapentin in pharmaceutical formulation.	2003 Feb 5	12560067
Photo-Fenton treatment of water containing natural phenolic pollutants.	2003 Jan	12656231
Potential inhibitors from wet oxidation of wheat straw and their effect on ethanol production of Saccharomyces cerevisiae: wet oxidation and fermentation by yeast.	2003 Mar 20	12529889

Patents

Sample Use Guides

In Vivo Use Guide

Mice: In in vivo antioxidant assay, mice were orally given a single dose (100 mg/kg) of vanillin. The highest activity in the plasma ORAC assay was observed at 5 min, when the concentrations of vanillin, vanillic acid, and protocatechuic acid were high.

Route of Administration: Oral

In Vitro Use Guide

Vanillin at 2.5 mM inhibited protein oxidation and lipid peroxidation induced by photosensitization with methylene blue plus light in rat liver mitochondria. It also exhibited hydroxyl radical and 2,2`-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS∙+) (IC50 value of 16.25 uM) scavenging activities. Pretreatment of vanillin (100 nM) also reduced rotenone induced mitochondrial dysfunction, oxidative stress, and apoptosis in SH-SY5Y neuroblastoma cells

Substance Class	Chemical Created by `admin` on `Wed Apr 02 13:29:58 GMT 2025` Edited by `admin` on `Wed Apr 02 13:29:58 GMT 2025`
Record UNII	CHI530446X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VANILLIN MELTING POINT STANDARD

Preferred Name

English

Vanillin

Official Name

English

VANILLALDEHYDE

Systematic Name

English

VANILLIN [MART.]

Common Name

English

4-HYDROXY-3-METHOXY-BENZYLDEHYDE

Common Name

English

NSC-403658

Code

English

VANILLIN, NATURAL [FHFI]

Common Name

English

FEMA NO. 3107

Code

English

METHYLPROTOCATECHUIC ALDEHYDE

Common Name

English

BENZALDEHYDE, 4-HYDROXY-3-METHOXY-

Systematic Name

English

VANILLIN [HSDB]

Common Name

English

VANILLIN [VANDF]

Common Name

English

VANILLIN [EP MONOGRAPH]

Common Name

English

NPLC-0145

Code

English

NSC-48383

Code

English

NSC-15351

Code

English

H-0264

Code

English

VANILLIN [FCC]

Common Name

English

VANILLIN [MI]

Common Name

English

VANILLIC ALDEHYDE

Common Name

English

VANILLIN [FHFI]

Common Name

English

4-HYDROXY-M-ANISALDEHYDE

Systematic Name

English

4-HYDROXY-3-METHOXYBENZALDEHYDE

Systematic Name

English

Vanillin [WHO-DD]

Common Name

English

LIOXIN

Brand Name

English

RHOVANIL

Common Name

English

VANILLIN [USP-RS]

Common Name

English

P-HYDROXY-M-METHOXYBENZALDEHYDE

Common Name

English

VANILLIN [II]

Common Name

English

3-METHOXY-4-HYDROXYBENZALDEHYDE

Systematic Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

115801