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%

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