Name | 2,4,5-Trimethoxybenzaldehyde |
Synonyms | Gazarin NCI-C61632 ASARALDEHYDE ASARONALDEHYDE Asarylaldehyde Azarylaldehyde 2,4,5-trimethyl ether 2,4,5-TRIMETHOXYBENZALDEHYDE 2,4,5-Trimethoxybenzaldehyde |
CAS | 4460-86-0 |
EINECS | 224-713-3 |
InChI | InChI=1/C10H12O4/c1-12-8-5-10(14-3)9(13-2)4-7(8)6-11/h4-6H,1-3H3 |
InChIKey | IAJBQAYHSQIQRE-UHFFFAOYSA-N |
Molecular Formula | C10H12O4 |
Molar Mass | 196.2 |
Density | 1.2166 (rough estimate) |
Melting Point | 112-114 °C (lit.) |
Boling Point | 140°C 4mm |
Flash Point | 140°C/4mm subl. |
Water Solubility | <0.1 g/100 mL at 22 ºC |
Solubility | Water solubility <0.1g/100 mL (22°C) |
Vapor Presure | 0.000125mmHg at 25°C |
Appearance | White-like crystal |
Color | White to light beige |
BRN | 1951403 |
Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
Sensitive | Air Sensitive |
Refractive Index | 1.5550 (estimate) |
MDL | MFCD00003312 |
Physical and Chemical Properties | Off-white crystals. Melting point 109-112 °c. |
Use | Used as a pharmaceutical intermediate for the preparation of asarone |
In vitro study | Asaraldehyde production is abundant, but not at all in its liquid medium as well as in its natural host, C. kanehirae wood. If cultured with acid-digested sawdust or vanillin from C. kanehirae wood, Asaraldehyde was produced in its medium. 100 mg/ml Asaraldehyde showed 3.32% prostaglandin H endoperoxide synthase -1 (COX-1) inhibitory activity, 52.69% of prostaglandin H endoperoxide synthase -2 (COX-2) inhibitory activity. 100 µg/mL of Asaraldehyde tended to inhibit the COX-2 enzyme. The inhibition ratio of Asaraldehyde to COX-2/COX-1 was 17.68 at 100 µg/mL compared to control. Asaraldehyde down-regulates the expression of C/EBPβ, C/ebpδ and C/EBPα, and inhibits the expression of PPARγ1, PPARγ2 and acetyl-coenzyme A carboxylase (ACC). |
Hazard Symbols | C - Corrosive |
Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R34 - Causes burns |
Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S27 - Take off immediately all contaminated clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
WGK Germany | 3 |
RTECS | CU8460000 |
TSCA | Yes |
HS Code | 29124990 |
Raw Materials | 1,4-Benzoquinone |
Reference Show more | 1. Dong Xiaoke, Liu Jinmin, Li Zhonghao, Yuan Siyuan, Wang Kaiyue, Li Lili, Zheng xiangchun. Study on the main blood components and pharmacokinetics of chaibei Zhixian decoction in rats [J]. Global Journal of Traditional Chinese Medicine, 2021,14(03):377-383. |
NIST chemical information | Information provided by: webbook.nist.gov (external link) |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
overview | 2,4, 5-trimethoxybenzaldehyde is mainly used to prepare asarone. Alpha-asarone mainly exists in the volatile oil of natural products such as Acorus calamus. It has sedative, hypnotic and antibacterial effects. It is clinically used for the treatment of chronic bronchitis, epilepsy, coma and other mental diseases. Since the 1960s, the extraction, synthesis, pharmacology, toxicology and clinic of α-asarone monomer, an effective component of Acorus plants, have been extensively studied at home and abroad, and significant progress has been made. |
biological activity | Asaraldehyde (Asaronaldehyde) is a natural COX-2 inhibitor, which is 17 times more selective than COX-1. |
Target | Value |
use | used for content determination/identification/pharmacological experiments, etc. Used as a pharmaceutical intermediate to prepare asarone |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |