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Osthole

CAS No.
484-12-8
Chemical Name:
Osthole
Synonyms
OSTHOL;Chuanxiongzine;Cnidium Monnieri Extract;Ostole;DaMiana Extract;Turnera Aphrodisiaca;Ostol;Cnidium;OSTHOLE;NSC 31868
CBNumber:
CB7454402
Molecular Formula:
C15H16O3
Molecular Weight:
244.29
MDL Number:
MFCD00076049
MOL File:
484-12-8.mol
Last updated:2024-01-10 17:27:35

Osthole Properties

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
Odor Type dry
Water Solubility 12mg/L(25 ºC)
λmax 322nm(MeOH)(lit.)
Merck 14,6895
InChIKey MBRLOUHOWLUMFF-UHFFFAOYSA-N
LogP 3.686 (est)
CAS DataBase Reference 484-12-8(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII XH1TI1759C
NIST Chemistry Reference Osthole(484-12-8)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319
Precautionary statements  P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330
WGK Germany  3
RTECS  GN7700000
HS Code  29322090

Osthole price More Price(59)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 78889 Osthole analytical standard 484-12-8 25mg $328 2022-05-15 Buy
Sigma-Aldrich 02150595 Osthole primary pharmaceutical reference standard 484-12-8 10mg $338 2022-05-15 Buy
TCI Chemical O0426 Osthole >98.0%(GC) 484-12-8 250mg $35 2024-03-01 Buy
TCI Chemical O0426 Osthole >98.0%(GC) 484-12-8 1g $87 2024-03-01 Buy
Cayman Chemical 19195 Osthole ≥98% 484-12-8 1g $138 2024-03-01 Buy
Product number Packaging Price Buy
78889 25mg $328 Buy
02150595 10mg $338 Buy
O0426 250mg $35 Buy
O0426 1g $87 Buy
19195 1g $138 Buy

Osthole Chemical Properties,Uses,Production

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 chemicalbook 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.

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.

Uses

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).

Indications

Impotence, infertility, uterine cold, wet nose with low back pain, vulva eczema, woman vulvae, trichomonas vaginitis

Definition

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

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.

673-22-3
484-12-8
Synthesis of Osthole from 2-Hydroxy-4-methoxybenzaldehyde
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View Lastest Price from Osthole manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
OSTHOLE pictures 2024-04-26 OSTHOLE
484-12-8
US $0.00-0.00 / kg 0.10000000149011612kg ≥99% 20tons Chongqing Zhihe Biopharmaceutical Co., Ltd.
Osthole pictures 2024-04-23 Osthole
484-12-8
US $0.00 / KG 1KG 10%-98% HPLC 1000KG` Changsha Staherb Natural Ingredients Co., Ltd.
Osthole pictures 2024-04-15 Osthole
484-12-8
US $1.00-1.00 / kg 1kg 99% 5ton/month ANHUI SHENGZHIKAI BIOTECHNOLOGY CO.,LTD
  • OSTHOLE pictures
  • OSTHOLE
    484-12-8
  • US $0.00-0.00 / kg
  • ≥99%
  • Chongqing Zhihe Biopharmaceutical Co., Ltd.
  • Osthole pictures
  • Osthole
    484-12-8
  • US $0.00 / KG
  • 10%-98% HPLC
  • Changsha Staherb Natural Ingredients Co., Ltd.
  • Osthole pictures
  • Osthole
    484-12-8
  • US $1.00-1.00 / kg
  • 99%
  • ANHUI SHENGZHIKAI BIOTECHNOLOGY CO.,LTD

Osthole Spectrum

Cnidiumfruitextract Osthol/Osthole Cnidium OSTHOLE(P) Epiandrosterone, 99%, HPLC Cnidiumlactone,Osthol 7-Methoxy-8-prenyl-2H-1-benzopyran-2-one 7-Methoxy-8-(3-methyl-2-buten-1-yl)-2H-chromen-2-one Osthenol Methylether Common Cnidium Fruit Extract Powder 7-Methoxy-8-(3-Methylbut-2-en-1-yl)-2H-chroMen-2-one NSC 31868 2H-1-Benzopyran-2-one, 7-methoxy-8-(3-methyl-2-butenyl)- 7-methoxy-8-(3-methyl-2-butenyl)-2h-1-benzopyran-2-on 7-Methoxy-8-(3-methyl-2-butenyl)-2H-chromen-2-one OSTHOLE AKOS 236-34 Cnidium lactone(OSTHOLE ) 7-methoxy-8-(3-methyl-2-butenyl)-coumari 7-Methoxy-8-(3-methyl-2-butenyl)-coumarin 7-Methoxy-8-isopentenylcoumarin Coumarin, 7-methoxy-8-(3-methyl-2-butenyl)- Coumarin, 7-methoxy-8-(3-mmtenyl)- Ostol 7-Methoxy-8-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one 7-METHOXY-8-(3-METHYL-BUT-2-ENYL)-CHROMEN-2-ONE 8-(3-METHYL-2-BUTENYL)HERNIARIN 2H-1-Benzopyran-2-one, 7-methoxy-8-(3-methyl-2-buten-1-yl)- Damiana p.e Osthole, >=98% Cnidium monnieric(L.)Cuss 7-methoxy-8-(3-methylbut-2-enyl)-1-benzopyran-2-one Cnidium Monnieri Extract (Standard) Osthole ointment Osthole CRS Osthole > Osthole USP/EP/BP Modified MRS Medium Base High Quality Cnidium Monnieri Extract 98% Osthole CAS 484-12-8 Osthole, >98%(GC) Osthole, 95%+ TIANFU-CHEM Osthole Osthole (NSC-31868) Osthole, 98%, from Cnidium monnieri (L.)Cuss. Common Cnidium Fruit Extract, Osthole fructus cnidii extract damiana/Osthole Osthole 484-12-8 Osthole, CP DaMiana Extract OSTHOL Chuanxiongzine Ostole Turnera Aphrodisiaca Cnidium Monnieri Extract Osthole osthol Damiana Leaf Extract Powder Snowparsley extract Cnidium extract