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HomeProduct name listOsthole

Osthole

Synonym(s):7-Methoxy-8-(3-methyl-2-butenyl)coumarin;7-Methoxy-8-isopentenylcoumarin;Osthol

  • CAS NO.:484-12-8
  • Empirical Formula: C15H16O3
  • Molecular Weight: 244.29
  • MDL number: MFCD00076049
  • EINECS: 1532714-185-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 23:02:33
Osthole Structural

What is Osthole?

Description

Cnidium is a Chinese medicine which is used widely by traditional medicine doctors. Cnidium has been recorded in almost all of the pharmaceutical monographs , including Shen Nong’s Classic Materia Medica, New Materia Medica, Compendium of Materia Medica, etc. Osthole is a major bioactivity compound of the Cnidium, which has the effect of dampness dispelling, insecticidal antipruritic,and aphrodisiac and is used for the treatment for pruritus and eczema, lumbago,kidney impotence, and infertility .
Osthole is derived from Umbelliferae and Rutaceae plants. Osthole is also distributed in Asteraceae and Leguminosae plants. Osthole is present in 14 genera of Umbelliferae plants: danggui (Angelica L.), gudanggui (Archangelica Hoffm.), mianguoqin (Cachrys L.), shechuang (Cnidium Cusson), awei (Ferula L.), duhuo (Heracleum L.), yanfeng (Libanotis Hill), ouqin (Petroselinum Hill), qianhu (Peucedanum L.), huiqin (Pimpinella L.), liangshechuang (Selinum L.). Shuanchiqin (Prangos Lindl), xifengqin (Seseli L.), oufangfeng (Pastinaca L.). Osthole is present in 17 genera of Rutaceae plants: ganju (Citrus L.), huangpi (Clausena Burm. F.), xiangju (Feronia Correa), jupanmu (Flindersia R. Br.), niyunxiang (Haplophyllum A. Juss.), mizhuyu (Melicope J. R. and G. Forst.), xiaoyunmu (Micromelum Bl.), jiulixiang (Murraya Koenig ex L.), zhi (Poncirus Raf.), yinyu (Skimmia Thunb.), Limonia, Myrtopsis, Pentaceras, Phebalium, Pilocarpus, Thamnosma, Ticorea) .

Physical properties

Appearance: white needlelike crystalline powder. Solubility: soluble in methanol. Melting point: 83–84 °C.

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.

The Uses of Osthole

Osthole inhibits the PI3K/Akt pathway thus inhibiting insulin-like growth factor-1 (IGF-1)-induced epithelial-to-mesenchymal transition (EMT) in brain cancer. Osthole may be used in the treatment of Glioblastoma multiforme (GBM).

What are the applications of Application

Osthole is an anticoagulant which inhibits phosphoinositide breakdown

Definition

ChEBI: A natural product found in Peucedanum ostruthium and Angelica pubescens.

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.

Properties of Osthole

Melting point: 83-84°C
Boiling point: 347.2°C (rough estimate)
Density  1.1263 (rough estimate)
refractive index  1.5570 (estimate)
storage temp.  Sealed in dry,2-8°C
solubility  methanol: soluble10mg/mL, clear, colorless
form  powder
color  white
Odor at 100.00 %. dry musty herbal
Water Solubility  12mg/L(25 ºC)
λmax 322nm(MeOH)(lit.)
Merck  14,6895
CAS DataBase Reference 484-12-8(CAS DataBase Reference)
NIST Chemistry Reference Osthole(484-12-8)

Safety information for Osthole

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313:IF SKIN irritation occurs: Get medical advice/attention.
P337+P313:IF eye irritation persists: Get medical advice/attention.

Computed Descriptors for Osthole

InChIKey MBRLOUHOWLUMFF-UHFFFAOYSA-N

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