484-12-8 Usage
Uses
Used in Pharmaceutical Industry:
Osthole is used as a pharmaceutical compound for its various therapeutic applications, including the treatment of pruritus, eczema, lumbago, kidney impotence, and infertility.
Used in Anticancer Applications:
Osthole is used as an anticancer agent, particularly in the treatment of Glioblastoma multiforme (GBM). It inhibits the PI3K/Akt pathway, thus preventing insulin-like growth factor-1 (IGF-1)-induced epithelial-to-mesenchymal transition (EMT) in brain cancer.
Used in Traditional Chinese Medicine:
Osthole is used in traditional Chinese medicine for its various health benefits, such as dampness dispelling, insecticidal antipruritic, and aphrodisiac effects.
Used in Plant Taxonomy:
Osthole is found in 14 genera of Umbelliferae plants and 17 genera of Rutaceae plants, making it a valuable compound for studying the taxonomy and classification of these plant families.
Plant extracts
Osthole is a substance extracted from the fruit of the annual Umbelliferae plant Fructus Cnidii. It appears as yellow-green to white crystalline powder. It is insoluble in cold water and petroleum ether, easily soluble in acetone, methanol, ethanol, chloroform and ethyl acetate and soluble in boiling petroleum ether. It has various effects including antispasmodic, hypotensive, anti-arrhythmic, enhancing immune function and broad-spectrum antimicrobial effect. It is clinically mainly used for the treatment of men impotence, scrotal wet itchy, women prurUus Yulvae and cold uterus and infertility, rheumatism, scabies, eczema and trichomonas vaginitis. Osthole can also be used to make field insecticides, fungicides with contact killing action being the primary effect and stomach poisoning being the auxiliary effect. The drug liquid can be absorbed through body surface and enter into the body and further act on the nervous system of pests, causing the non-functional muscle contraction of the pests and eventually leading to death due to energy exhaustion. It has a relative excellent contact-killing effect on various kinds of pests such as cabbage caterpillar, tea looper, cotton bollworm, beet armyworm and any kinds of aphids.
Physical and Chemical Properties
Osthole belongs to coumarin compounds. It is prismatic-like crystals (diethyl ether) and needle-like crystals (Ethanol) with the melting point being 83~84 ℃ and the boiling point being 145~150 ℃. It is soluble in alkaline solution, methanol, ethanol, chloroform, acetone, ethyl acetate, and boiling petroleum ether but insoluble in water and petroleum ether.
Pharmacological effects
Osthole has various kinds of effects of antispasmodic, hypotensive, anti-arrhythmic and enhancing immune function and broad-spectrum antimicrobial effect. Osthole can not only have efficacy such as anti-hypertensive, anti-arrhythmic, anti-inflammatory, anti-tumor and anti-osteoporosis effect, but can also act as a new type of biological pesticides with significant efficacy in treating pests and plant pathogens.
The above information is edited by the lookchem of Dai Xiongfeng.
Botanical insecticides
Osthole is a class of natural coumarin compound which had been initially extracted from Umbelliferae plants. The dried ripe fruit of Fructus Cnidii in the Umbelliferae plant, Cnidium monnieri has a relative high content, hence obtaining the name. Related research has shown that Osthole is also presented in other kinds of plants, including Umbelliferae including Angelica, Archangelica Hoffm and Cnidium as well as rutaceous plant such as citrus, clausena, Limonia acidissima and Haplophyllum A. Juss. In addition, it is also distributed in a few species of Asteraceae and legumes.
Osthole has its chemical name being 7-methoxy-8-isopenteylcoumarin with the core structure consisting of benzene and pyrone ring. As a member of coumarins compounds, Osthole, in addition to containing the core structure of coumarin, also has isopentenyl structure. Compound containing isopentenyl structure, as a phytoalexin, plays an important role in fighting against disease.
Osthole, as a kind of botanical pesticide, has contact-killing effect being the primary effect and stomach poisoning effect being the auxiliary effect. The drug liquid can be absorbed into the insect body through body surface and acts on the nervous system of pests, causing non-functional muscle contraction and final death due to energy exhaustion. Indoor activity virulence tests have showed that it has a higher activity against Pieris rapae (LD50 is 6.2258 mg/kg). It is demonstrated through the field efficacy trials that it has excellent efficacy in the treatment of Pieris rapae of cruciferous vegetables and tea and tea looper caterpillar. The drug dosage for prevention and treatment of the Pieris rapae of cruciferous vegetables has the active ingredient be 4.8~7.2g/hm (equals to 80~120 mL per acre if converted to 0.4% Osthole cream commercialized product); the drug dosage against tea mites has the active ingredient be 6 to 7.2 g/hm (equals to 100~120 mL per acre if converted to 0.4% Osthole cream commercialized product). Apply the drug liquid at an amount of 50~75 kg per acre with uniform spray; the period of validity is about 7d. It is safe for crop within the dose range with no drug injury.
History
Cnidium is a Chinese medicine which is used widely by traditional medicine doctors.
Osthole was isolated in 1950 and then its chemical structure was determined
. Osthole can be extracted by solvent method, acid-base method,
ultrasound, and supercritical and other methods. The main methods for the separation
of osthole are recrystallization, chromatography, and so on. With the development
of modern pharmacological experimental methods and techniques, the
pharmacological effects of osthole have been discovered and developed. It is found
that osthole has many pharmacological activities such as anti-osteoporosis, antiplatelet
aggregation, antiviral, anti-mutation, anti-allergic reaction, and so on. In
recent years, it has been found that osthole has obvious antitumor activity. In addition,
osthole also has strong insecticidal and antifungal effects. In the future, osthole
is expected to be developed as a new kind of low-toxicity, high-efficiency, and lowresidue
pesticide.
Indications
Impotence, infertility, uterine cold, wet nose with low back pain, vulva eczema,
woman vulvae, trichomonas vaginitis
Pharmacology
1. Osthole can enhance the non-specific immune function of mice.
2. Osthole exhibits protective effect on the heart and circulatory system. Osthole
can dilate blood vessels, reduce blood pressure, reduce blood lipid, and inhibit
the formation of venous thrombosis.
3. Osthole has a central sedative effect and can improve the learning and memory
function of mice.
4. Osthole presents the effect of relieving asthma by regulating the function of
hypothalamus-pituitary-adrenal cortex system.
5. Osthole has antiaging and antioxidant effects, which may be related to the
direct scavenging of oxygen free radicals.
6. Osthole reduces osteoporosis and bone resorption in ovariectomized rats and
increases bone mass. Osthole can effectively prevent osteoporosis in ovariectomized
rats, prevent bone loss, and maintain bone metabolism balance.
7. Osthole can relieve itching, which may be related to blocking the Ca2+ channel
of mast cells, decreasing the flow of Ca2+, and inhibiting the release of histamine
from mast cells.
8. Osthole is a noncompetitive antagonist of Ca2+, which can inhibit the smooth
muscle of the uterus. In addition, osthole has a certain androgen-like, estrogen-like
effect.
9. Osthole has anti-inflammatory effects on acute and chronic inflammation models,
and its anti-inflammatory mechanism is not through the pituitary-adrenal cortex system, but also with the synthesis of PGE. It may be possible to exert anti-inflammatory effects by enhancing non-specific immune function and/or anti-allergic reactions .
10. Accumulating experimental evidences have shown that osthole exhibited antiproliferative properties and induced apoptosis in various kinds of tumor cells.
Besides, osthole has broad-spectrum antibacterial and insecticidal effects.
Clinical Use
In vitro and in vivo experimental results have revealed that osthole demonstrates
multiple pharmacological actions including neuroprotective, osteogenic, immunomodulatory,anticancer, hepatoprotective, cardiovascular protective, and antimicrobial activities. Osthole is expected to be used in the treatment of cardiovascular system, central nervous system, and immune system diseases.
Check Digit Verification of cas no
The CAS Registry Mumber 484-12-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,8 and 4 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 484-12:
(5*4)+(4*8)+(3*4)+(2*1)+(1*2)=68
68 % 10 = 8
So 484-12-8 is a valid CAS Registry Number.
InChI:InChI=1/C15H16O3/c1-10(2)4-7-12-13(17-3)8-5-11-6-9-14(16)18-15(11)12/h4-6,8-9H,7H2,1-3H3
484-12-8Relevant articles and documents
Palladium-catalyzed synthesis of 8-allyl or 8-prenylcoumarins by using organotin reagents as multicoupling nucleophiles
Yin, Qiang,Yan, Han,Zhang, Yaqin,Wang, Yige,Zhang, Guojin,He, Yuxiang,Zhang, Weihua
, p. 85 - 88 (2013)
In this study, 8-iodocoumarin derivatives underwent a direct Stille cross-coupling reaction with several organotin compounds in the presence of a catalytic amount of Pd(PPh3)4 in DMF at 80 °C. The cross-coupling reaction proceeded smoothly under mild conditions and permitted the formation of 8-allyl or 8-prenylcoumarin compounds in good yields. Copyright
Practical, Large-Scale Preparation of Benzoxepines and Coumarins through Rhodium(III)-Catalyzed C-H Activation/Annulation Reactions
Gulías, Moisés,Marcos-Atanes, Daniel,Mascare?as, José L.,Font, Marc
supporting information, p. 1669 - 1673 (2019/09/04)
Herein we disclose the assembly of benzoxepines and coumarins from 2-alkenylphenol precursors using [Cp*RhCl2]2 as the precatalyst and alkynes or carbon monoxide as reacting partners. The preparation of benzoxepines and coumarins can be scaled up to 33 mmol using low catalyst loadings.
Microwave-Assisted Synthesis of Phenylpropanoids and Coumarins: Total Synthesis of Osthol
Konrádová, Daniela,Kozubíková, Hana,Dole?al, Karel,Pospí?il, Ji?í
, p. 5204 - 5213 (2017/09/29)
Herein we describe a one-pot microwave-assisted method for the synthesis of cinnamic acid and coumarin derivatives. The synthesis begins with an aldehyde synthon, and the chosen reaction conditions determine whether a cinnamic acid or coumarin derivative is formed. A regioselective Claisen rearrangement was also efficiently incorporated into the synthetic sequence to further increase the complexity of the product. Notably, this approach provides high product yields and selectivities without the need of a phenol protecting group.
Synthesis of Allyl- and Prenylcoumarins via Microwave-Promoted Tandem Claisen Rearrangement/Wittig Olefination
Schmidt, Bernd,Riemer, Martin
, p. 141 - 149 (2015/12/26)
Allyl, dimethylallyl, crotyl, and prenyl ethers of various aromatic ortho-hydroxy carbonyl compounds undergo a tandem sequence of Claisen rearrangement, carbonyl olefination, and cyclization upon microwave irradiation in the presence of a stabilized ylide. The products are multiply substituted 6- or 8-allylated or prenylated coumarins (2H-chromen-2-ones).
Synthesis of osthole derivatives with grignard reagents and their larvicidal activities on mosquitoes
Liu, Ming,Liu, Yang,Hua, Xuewen,Wu, Changchun,Zhou, Sha,Wang, Baolei,Li, Zhengming
, p. 1353 - 1358 (2016/02/18)
The structure of osthole has been modified to improve its larvicidal activity against mosquitoes. A new efficient synthesis of osthole derivatives with Grignard reagents has been developed, which employs CuI and LiCl as promoters and covers a broad range of substrates to afford the corresponding products in mild to good yields (up to 83%). Bio-activity evaluation showed that several products exhibited better activities than osthole. CuI and LiCl promoted efficient synthesis of osthole derivatives with Grignard reagents has been developed. Bio-activity evaluation showed that several products exhibited far better larvicidal activities against mosquitoes than osthole.
Synthesis and anthelmintic activity of osthol analogs against Dactylogyrus intermedius in goldfish
Liu, Guang-Lu,Hao, Bing,Liu, Shao-Peng,Wang, Gao-Xue
, p. 582 - 590 (2012/09/11)
In an attempt to develop novel anthelmintic agents, our previously isolated osthol was used as lead structures for further optimization. In our research, a series of coumarin analogs, prepared from 7-hydroxy coumarin or 7-hydroxy-4-methyl coumarin, have been evaluated for their anthelmintic activities. In all of the compounds, 6 and 7 were first synthesized, and their structures were identified based on NMR and MS values. Among the candidates, 8-allyl-7-allyloxycoumarin showed better anthelmintic activity than other compounds against Dactylogyrus infestation with EC50 value of 1.81 mg/L. The quantitative structure-activity relationship (QSAR) of 16 osthol analogs with anthelmintic activity expressed as pEC50 and toxicity to goldfish expressed pLC50, such results can offer useful theoretical references for future experimental works.
