Isovanillin

Names

[ CAS No. ]:
621-59-0

[ Name ]:
Isovanillin

[Synonym ]:
Benzaldehyde, 3-hydroxy-4-methoxy-
4-MeO-3-OHC6H3CHO
3-hydroxy-4-methoxy-benzaldehyde
Isovanillin
ISOVANILIN
3-Hydroxy-p-anisaldehyde
4-08-00-01764 (Beilstein Handbook Reference)
Isovanilline
p-Anisaldehyde, 3-hydroxy- (8CI)
3-Hydroxy-4-methoxybenzolcarbaldehyd
3-Hydroxy-4-methoxybenzaldehyde
4-methoxy-3-hydroxybenzaldehyde
EINECS 210-694-9
p-Anisaldehyde, 3-hydroxy-
VHR CQ DO1
Isovanicaline
MFCD00003369
5-Formylguaiacol
iso-vanillin
Isovanilllin

Biological Activity

[Description]:

Isovanillin is an aldehyde oxidase inhibitor[1]. Antispasmodic activities[2]. Antidiarrheal activities[3].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Metabolic Disease

Research Areas >> Neurological Disease

Natural Products >> Phenols

[Target]

Aldehyde oxidase[1]

[In Vitro]

Isovanillin is not a substrate for aldehyde oxidase and therefore it is metabolized to isovanillic acid predominantly by aldehyde dehydrogenase[1]. Isovanillin is relaxant of ileum contractions induced by 5-HT (IC50=356±50μM) [2].

[In Vivo]

Isovanillin (2 mg/kg & 5 mg/kg) and iso-acetovanillon (2 mg/kg & 5 mg/kg) both have antidiarrheal and anti-motility effect on gastrointestinal tract[3].

[References]

[1]. Panoutsopoulos GI, et al. Enzymatic oxidation of vanillin, isovanillin and protocatechuic aldehyde with freshly prepared Guinea pig liver slices. Cell Physiol Biochem. 2005;15(1-4):89-98.

[2]. Sadraei H, et al. Antispasmodic activity of isovanillin and isoacetovanillon in comparison with Pycnocycla spinosa Decne.exBoiss extract on rat ileum. Res Pharm Sci. 2014 May-Jun;9(3):187-92.

[3]. Sadraei H, et al. Antidiarrheal activities of isovanillin, iso-acetovanillon and Pycnocycla spinosa Decne ex.Boiss extract in mice. Res Pharm Sci. 2014 Mar-Apr;9(2):83-9.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
308.1±0.0 °C at 760 mmHg

[ Melting Point ]:
113-116 °C

[ Molecular Formula ]:
C₈H₈O₃

[ Molecular Weight ]:
152.147

[ Flash Point ]:
119.9±15.3 °C

[ Exact Mass ]:
152.047348

[ PSA ]:
46.53000

[ LogP ]:
1.10

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.588

[ Storage condition ]:
-20°C Freezer, Under Inert Atmosphere

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CU6540000

CHEMICAL NAME :: Benzaldehyde, 3-hydroxy-4-methoxy-

CAS REGISTRY NUMBER :: 621-59-0

BEILSTEIN REFERENCE NO. :: 1073021

LAST UPDATED :: 199701

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C8-H8-O3

MOLECULAR WEIGHT :: 152.16

WISWESSER LINE NOTATION :: VHR CQ DO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1276 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1470 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Human Lymphocyte

DOSE/DURATION :: 1500 umol/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 206,17,1988

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36/37

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
CU6540000

[ HS Code ]:
29124900

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2912499000

[ Summary ]:
2912499000. other aldehyde-ethers, aldehyde-phenols and aldehydes with other oxygen function. VAT:17.0%. Tax rebate rate:9.0%. . MFN tariff:5.5%. General tariff:30.0%

Articles

Synthesis and accumulation of aromatic aldehydes in an engineered strain of Escherichia coli.

J. Am. Chem. Soc. 136(33) , 11644-54, (2014)

Aromatic aldehydes are useful in numerous applications, especially as flavors, fragrances, and pharmaceutical precursors. However, microbial synthesis of aldehydes is hindered by rapid, endogenous, an...

3D-QSAR and molecular docking studies of benzaldehyde thiosemicarbazone, benzaldehyde, benzoic acid, and their derivatives as phenoloxidase inhibitors.

Bioorg. Med. Chem. 15 , 2006-15, (2007)

Phenoloxidase (PO), also known as tyrosinase, is a key enzyme in insect development, responsible for catalyzing the hydroxylation of tyrosine into o-diphenols and the oxidation of o-diphenols into o-q...

Systemic exposure to and disposition of catechols derived from Salvia miltiorrhiza roots (Danshen) after intravenous dosing DanHong injection in human subjects, rats, and dogs.

Drug Metab. Dispos. 43(5) , 679-90, (2015)

DanHong injection is a Danshen (Salvia miltiorrhiza roots)-based injectable solution for treatment of coronary artery disease and ischemic stroke. Danshen catechols are believed to be responsible for ...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.