3-Methoxysalicylaldehyde

Names

[ CAS No. ]:
148-53-8

[ Name ]:
3-Methoxysalicylaldehyde

[Synonym ]:
2-Hydroxy-3-(methyloxy)benzaldehyde
ORTHO-VANILLIN
VHR BQ CO1
Benzaldehyde, 2-hydroxy-3-methoxy-
2-Hydroxy-m-anisaldehyde
EINECS 205-715-3
o-Vanillin
3-Methoxysalicylaldehyde
MFCD00003322
2-Hydroxy-3-methoxybenzaldehyde

Biological Activity

[Description]:

o-Vanillin (2-Vanillin) is a nature product, could be extracted from Vanilla planifolia, Pinus koraiensis fruit. o-Vanillin is a potent antifungal agent. o-Vanillin inhibits the growth of mycelia by disrupting the integrity of cell walls and cell membranes. o-Vanillin inhibits Doxorubicin (HY-15142A)- and 4-hydroperoxycyclophosphamide-induced NF-κB activation[1][2].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

[In Vitro]

o-Vanillin (2-Vanillin; 0-125 μg/mL; 24-72 h) inhibits the mycelial growth of A. flavus in a dose-dependent manner[1]. o-Vanillin (0-100 μg/mL; 48 h; A. flavus) changes the morphology of mycelia and induces irregular shrinkage of the mycelia[1]. o-Vanillin (0-100 μg/mL; A. flavus) decreases the protein content of the cell wall surface and the content of β-1,3-glucan[1]. o-Vanillin (0-100 μg/mL; A. flavus) destroys cell membrane integrity. o-Vanillin releases cell constituents and decreases extracellular pH value[1]. o-Vanillin (0-100 μg/mL) could effectively inhibit the growth of A. flavus on corn kernels[1]. o-Vanillin (0-250 μM) inhibits doxorubicin-mediated induction of NFĸB activity by 65% in A375/NFĸB-Luc cells. o-Vanillin suppresses 4-HC-induced activity by 43%[2].

[In Vivo]

o-Vanillin (2-Vanillin; 60 mg/kg; p.o.; daily, for 5 d) inhibits tumor growth in mice bearing A375 human melanoma xenografts[2]. Animal Model: Male NSG mice with A375 human melanoma xenografts (12-16 weeks of age)[2] Dosage: 60 mg/kg Administration: Oral administration; daily, for 5 days Result: Delayed the growth of A375 human melanoma xenografts in immunodeficient NSG mice.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
265.5±0.0 °C at 760 mmHg

[ Melting Point ]:
40-42 °C(lit.)

[ Molecular Formula ]:
C₈H₈O₃

[ Molecular Weight ]:
152.147

[ Flash Point ]:
94.0±15.3 °C

[ Exact Mass ]:
152.047348

[ PSA ]:
46.53000

[ LogP ]:
1.40

[ Vapour Pressure ]:
0.0±0.5 mmHg at 25°C

[ Index of Refraction ]:
1.588

[ Water Solubility ]:
slightly soluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CU6530000

CHEMICAL NAME :: Benzaldehyde, 2-hydroxy-3-methoxy-

CAS REGISTRY NUMBER :: 148-53-8

BEILSTEIN REFERENCE NO. :: 0471913

LAST UPDATED :: 199701

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C8-H8-O3

MOLECULAR WEIGHT :: 152.16

WISWESSER LINE NOTATION :: VHR BQ CO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 20,563,1982

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 20,573,1982

TYPE OF TEST :: Rinsed with water

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 20,573,1982 ** ACUTE TOXICITY DATA **

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 347 mg/kg

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

REFERENCE :: COREAF Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. (Paris, France) V.1-261, 1835-1965. For publisher information, see CRASEV. Volume(issue)/page/year: 243,609,1956

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1330 mg/kg

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

REFERENCE :: IJANDP International Journal of Andrology. (Scriptor Publisher ApS, 15 Gasvaerksvej, DK-1656 Copenhagen V, Denmark) V.1- 1978- Volume(issue)/page/year: 10,741,1987

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory stimulation

REFERENCE :: COREAF Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. (Paris, France) V.1-261, 1835-1965. For publisher information, see CRASEV. Volume(issue)/page/year: 238,2576,1954

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 430 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory stimulation

REFERENCE :: COREAF Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. (Paris, France) V.1-261, 1835-1965. For publisher information, see CRASEV. Volume(issue)/page/year: 238,2576,1954

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory stimulation

REFERENCE :: COREAF Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. (Paris, France) V.1-261, 1835-1965. For publisher information, see CRASEV. Volume(issue)/page/year: 238,2576,1954

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-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 ]:
S23-S36-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
CU6530000

[ 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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Related Compounds

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