Syringaldehyde

Names

[ CAS No. ]:
134-96-3

[ Name ]:
Syringaldehyde

[Synonym ]:
EINECS 205-167-5
Syringic Aldehyde
4-Hydroxy-3,5-dimethoxybenzaldehyde
4-Hydroxy-3,5-dimethoxybenzolcarbaldehyd
Syringaldehyde
3,5-Dimethoxy-4-Hydroxybenzaldehyde
Benzaldehyde, 4-hydroxy-3,5-dimethoxy-
MFCD00006943

Biological Activity

[Description]:

Syringaldehyde is a polyphenolic compound belonging to the group of flavonoids and is found in different plant species like Manihot esculenta and Magnolia officinalis[1]. Syringaldehyde moderately inhibits COX-2 activity with an IC50 of 3.5 μg/mL[2]. Anti-hyperglycemic and anti-inflammatory activities[1].

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> COX

Natural Products >> Flavonoids

Research Areas >> Inflammation/Immunology

Research Areas >> Metabolic Disease

[Target]

COX-2:19.2 μM (IC50)

[In Vitro]

Syringaldehyde inhibits COX-2 activity in a dosedependent manner with an IC50 of 3.5 μg/mL[2].

[In Vivo]

Syringaldehyde exerts anti-hyperglycemic effect in rat model of diabetes induced by streptozotocin. Apart from antioxidant capability, Syringaldehyde also has anti-inflammatory activity as it is found to have inhibitory action on cyclo-oxygenase 2 (COX-2) in mouse macrophage cell line[1].

[Animal admin]

Rats[1] Adult male albino wistar rats (weighing 180-220 g) 12.5 mg/kg, 25 mg/kg, and 50 mg/kg; p.o.; for 21 days Adult male albino wistar rats are randomly divided into six groups (n=6), first group serves as control and receives vehicle (orally) for 21 days. Second group is given Syringaldehyde in saline orally at 50 mg/kg for 21 days. Third group receives vehicle for a period of 21 days and then ISO (100 mg/kg, s.c.) on 20th and 21 st day at an interval of 24 h. Fourth group is given Syringaldehyde for 21 days at 12.5 mg/kg, p.o. and ISO on 20th and 21 st day. Fifth group receives Syringaldehyde at concentration of 25 mg/kg, p.o. for 21 days and ISO on 20th and 21 st day. The sixth group is treated with 50 mg/kg of Syringaldehyde for 21 days and ISO on 20th and 21 st day. During the experimental procedure body weight of animals are monitored and on 22nd day, 24 h after second injection of ISO, rats sre sacrificed by cervical decapitation. Note: Body weight of animals belonging to different groups did not differed significantly but heart weight of ISO challenged animals were highly elevated (p ≤ 0.05) than control rats. However, treatment of rats with Syringaldehyde significantly reduced heart weight in dose dependent way. The rats treated with Syringaldehyde alone displayed an insignificant difference from control group.

[References]

[1]. Shahzad S, et al. Protective effect of syringaldehyde on biomolecular oxidation, inflammation and histopathological alterations in isoproterenol induced cardiotoxicity in rats. Biomed Pharmacother. 2018 Dec;108:625-633.

[2]. Stanikunaite R, et al. Cyclooxygenase-2 inhibitory and antioxidant compounds from the truffle Elaphomyces granulatus. Phytother Res. 2009 Apr;23(4):575-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
322.1±37.0 °C at 760 mmHg

[ Melting Point ]:
110-113 °C(lit.)

[ Molecular Formula ]:
C₉H₁₀O₄

[ Molecular Weight ]:
182.173

[ Flash Point ]:
130.1±20.0 °C

[ Exact Mass ]:
182.057907

[ PSA ]:
55.76000

[ LogP ]:
0.86

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.568

[ Water Solubility ]:
very sparingly soluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CU5760000

CHEMICAL NAME :: Benzaldehyde, 3,5-dimethoxy-4-hydroxy-

CAS REGISTRY NUMBER :: 134-96-3

BEILSTEIN REFERENCE NO. :: 0784514

LAST UPDATED :: 199701

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C9-H10-O4

MOLECULAR WEIGHT :: 182.19

WISWESSER LINE NOTATION :: VHR DQ CO1 EO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex)

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 7,178,1964

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 ]:
S26-S37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
CU5760000

[ Packaging Group ]:
I; II; III

[ 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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