56505-80-7

Basic information

• Product Name: 3-oxododecanal
• Synonyms: 3-oxododecanal;Dodecanal, 3-oxo-
• CAS NO: 56505-80-7
• Molecular Formula: C12H22O2
• Molecular Weight: 198.3
• Mol File: 56505-80-7.mol

Chemical Properties

• Boiling Point: 277.8°Cat760mmHg
• Flash Point: 103.2°C
• Appearance: /
• Density: 0.897g/cm³
• Vapor Pressure: 0.00443mmHg at 25°C
• Refractive Index: 1.436
• PKA: 5.91±0.23(Predicted)
• CAS DataBase Reference: 3-oxododecanal(CAS DataBase Reference)
• NIST Chemistry Reference: 3-oxododecanal(56505-80-7)
• EPA Substance Registry System: 3-oxododecanal(56505-80-7)

Safety Data

• Hazardous Substances Data: 56505-80-7(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
3-oxododecanal is used as a fragrance ingredient for its strong, distinctive scent. Its ability to easily polymerize allows for the creation of a variety of complex and long-lasting fragrances.
Used in Flavor Industry:
In the flavor industry, 3-oxododecanal is used as a flavoring agent to impart a unique taste to various food and beverage products. Its strong aromatic properties make it a valuable addition to the flavorist's toolbox.
Used in Traditional Chinese Medicine:
3-oxododecanal, as a component of Houttuynia cordata Thunb (also known as yuxingcao 鱼腥草), is used in traditional Chinese medicine for its various therapeutic properties. It is employed in the treatment of skin diseases, hemorrhoids, and certain women's diseases, as well as for relieving fever, resolving toxicity, reducing swelling, draining pus, and promoting urination.
Used in Pharmaceutical Industry:
Due to its presence in Houttuynia cordata Thunb, 3-oxododecanal may also have potential applications in the pharmaceutical industry for the development of new drugs and treatments, particularly in the areas of skin care, anti-inflammatory, and antiseptic products.

History

In 1952, houttuynin was firstly found in the volatile oil extracted from Houttuynia by steam distillation. The chemical structure was named decanoyl acetaldehyde. However, houttuynin is easy to polymerize and became invalid. In 1971, Chinese scholars synthesized sodium houttuyfonate (houttuyninum, HOU), which is an addition compound of sodium bisulfite and houttuynin. HOU is more stable and maintains the original antibacterial activity. HOU possessed broad-spectrum antibacterial and anti-inflammatory activities, diuretic swelling, rapid antifebrile, antivirus and antitumor proliferation, increased immunity, and other pharmacological effects.Neo-houttuyninum as the other derivative of houttuynin possesses more obvious inhibitory effect on a variety of bacteria and is used for the treatment of infectious diseases.Since houttuynin was found 60? years ago, Houttuynia injection preparations have been developed, such as Houttuynia injection, neo-houttuyfonate sodium chloride injection, neo-houttuyfonate injection, etc. These drugs are commonly used in clinical antimicrobial drugs. However, these injection preparations were withdrawed for serious adverse reactions in 2006, and continued to be used in clinic since 2008.

Indications

Houttuynin is recorded in the Pharmacopoeia of the People’s Republic of China (1995).Houttuynin preparations include Houttuynia injection, sodium neo-houttuyfonate injection, sodium neo-houttuyfonate and sodium chloride injection, sodium houttuyfonate tablets, and tabellae natrii houttuyfonatis. These preparations are mainly used to treat chronic bronchitis, pediatric pneumonia, and other respiratory inflammatory diseases; cervicitis, annex inflammation, pelvic inflammatory disease, chronic cervicitis, and other gynecological inflammation; and also other skin diseases such as psoriasis. Houttuynin preparations also include sodium houttuyfonate suppository and compound Houttuynia tablets. The former is used to treat cervical erosion, and the latter is used to treat acute pharyngitis and acute tonsillitis.

Pharmacology

Houttuynin is reported as a major antibacterial constituent in the volatile oil of H. cordata. Houttuynin exhibits significant inhibitory effects on Staphylococcus aureus, pneumococcus, and other bacteria as well as certain fungi and also has certain antiviral and anti-inflammatory effects. It is reported that houttuynin could reduce cardiomyocyte cross-section area and collagen deposition. Houttuynin attenuates ventricular remodeling in coronary artery ligation rats by restricting the excessive activation of rennin-angiotensin-aldosterone system (RAAS) and peroxidation . Houttuynin also shows hypolipidemic and anti-atherosclerotic effects.Houttuyninum has a significant inhibitory effect on Candida albicans, Cryptococcus neoformans, and Brochothrix thermosphacta. Houttuyninum has anti-inflammatory and analgesic effects, and the inhibition of inflammation is related to NF-κB and MCP-1. In recent years, studies have shown that intragastric administration of houttuyninum can increase apoptosis of the rheumatoid arthritis synovial cell and reduce joint index and inflammation factor levels in rheumatoid arthritis rat model

Clinical Use

Houttuynin and its derivatives are used to treat milk moths, lung carbuncle, leaching disease, carbuncle swollen sore, and other infectious diseases. Currently it is used mainly for the treatment of gynecological diseases and respiratory system, especially upper respiratory tract infection. However, there are side effects associated with the use of these injection preparations, mainly involving the cardiovascular system, gastrointestinal system, blood system, and skin or kidney.

InChI:InChI=1/C12H22O2/c1-2-3-4-5-6-7-8-9-12(14)10-11-13/h11H,2-10H2,1H3

Upstream product

• 112-12-9 methyl nonyl ketone 
• 109-94-4 formic acid ethyl ester 
• 111-83-1 1-bromo-octane 
• 41125-09-1 3-oxo-butyraldehyde; sodium enolate 

Relevant articles and documents

Development and verification of a precolumn derivatization lc-ms/ms method for the pharmacokinetic study of houttuynine of houttuynia essential oil

Houttuynia essential oil (HEO) has excellent antiviral, anti-inflammatory, and other phar-macological effects, but the lack of effective analytical methods to quantify HEO in plasma has hindered its better clinical monitoring. Houttuynine (Hou) is one of the main active ingredients and quality control substances of HEO, so the pharmacokinetic study of HEO could be conducted by determining Hou blood concentration. Hou is active and not stable in plasma, which makes its blood concentration difficult to measure. In this work, a novel liquid chromatography tandem mass spectrometry (LC-MS/MS) method for Hou determination in rat blood was established that involves Hou being derivatized with 2, 4-dinitrophenylhydrazine to form a stable compound to prevent degradation. Herein, p-Tolualdehyde-2,4-dinitrophenylphenylhydrazone was selected as an internal standard substance and the LC-MS/MS method was evaluated for selectivity, precision, accuracy, calibration limit, matrix effect, recovery, and stability. Good linearity (r2 = 0.998) was reached in the range of 2–2000 ng/mL, and the lower limit of quantification of Hou was determined to be 2 ng/mL. The mean intra-assay accuracy ranged from 77.7% to 115.6%, whereas the intra-assay precision (relative standard deviation, RSD) was below 11.42%. The matrix effect value for Hou in rat plasma was greater than 75%, and for the internal standard (IS) it was 104.56% ± 3.62%. The extraction recovery of Hou were no less than 90%, and for the IS it was 96.50% ± 4.68%. Our method is sensitive and reliable and has been successfully applied to the pharmacokinetic analysis of Hou in rats given HEO via gavage and injection.