66-97-7
psoralen
CAS: 66-97-7
Molecular Formula: C11H6O3
66-97-7 - Names and Identifiers
| Name | psoralen |
| Synonyms | psoralen PSORALEN Furo(4',5',6,7)coumarin furo(2',3',7,6)coumarin Fructus Psoraleae extract 7H-furo[3,2-g]chromen-7-one Psoralea corylifolia Linn. Extract TGRRRRRRRRRRRRRRRRRRRRRRRRRRRRRRRRRRRY MJJNNNNNNN |
| CAS | 66-97-7 |
| EINECS | 200-639-7 |
| InChI | InChI=1/C11H6O3/c12-11-2-1-7-5-8-3-4-13-9(8)6-10(7)14-11/h1-6H |
| InChIKey | ZCCUUQDIBDJBTK-UHFFFAOYSA-N |
66-97-7 - Physico-chemical Properties
| Molecular Formula | C11H6O3 |
| Molar Mass | 186.16 |
| Density | 1.2477 (rough estimate) |
| Melting Point | 160-162°C |
| Boling Point | 280.64°C (rough estimate) |
| Flash Point | 173.1°C |
| Water Solubility | 65.16mg/L(25 ºC) |
| Solubility | Soluble in ethanol, chloroform, slightly soluble in water, ether and petroleum ether. |
| Vapor Presure | 1.91E-05mmHg at 25°C |
| Appearance | Colorless needle crystal |
| Color | White to Off-White |
| Maximum wavelength(λmax) | ['328nm(EtOH)(lit.)'] |
| Merck | 14,7928 |
| BRN | 152784 |
| Storage Condition | 2-8°C |
| Sensitive | Sensitive to heat and light |
| Refractive Index | 1.6310 (estimate) |
| MDL | MFCD00010520 |
| Physical and Chemical Properties | Psoralea corylifolia L. Fruit from legume Psoralea |
66-97-7 - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| RTECS | LV0944000 |
| FLUKA BRAND F CODES | 8-10 |
| HS Code | 29339900 |
66-97-7 - Reference
| Reference Show more | 1. Yang, Jie-Fang. Simultaneous determination of six main components in gukang capsules by LC-MS [J]. China pharmacy 2012 23(35):3344-3346. 2. Fan Binbing, Guo Yinhua, Huang Ting. Evaluation of processing technology of Psoralea corylifolia based on tissue distribution characteristics [J]. Journal of Liaoning University of Traditional Chinese Medicine, 2019, 21(02):58-60. 3. Zhang Na, Liu Chuanxin, Zhang chenning, etc. Mechanism of Hepatotoxicity induced by Psoralea corylifolia L. Combined with UPLC-QTOF-MS and network toxicology techniques [J]. International Journal of Pharmaceutical Research, Vol. 47, No. 5, 2020, pp. 370-376, ISTIC PKU CSCD, 2020. 4. Simultaneous determination of 12 kinds of methoxyflavonoids and coumarins in citrus juice by Li Guijie, Tan Xiang, Wang Hua, Wu Houyan, Russell ROUSEFF.HPLC-DAD-FLD [J]. Food Science, 2017, 38(20):112-118. 5. Cao Shuli Zhao Chunjie Cai Li Xia Jing Minqi Li Yibai. Simultaneous determination of psoralen, isopsoralen, atractylenolide Ⅲ and isoimperatorin in Shenling Baizhu powder by UPLC [J]. Journal of Shenyang Pharmaceutical University 2018 35(07):568-573. 6. Zheng Nan, Guo Yihua, Liu Diao, et al. Study on fingerprint of different processed products of Psoralea corylifolia L. [J]. Liaoning Journal of Traditional Chinese Medicine, 2015(04):157-159. 7. Xiaofen Liu, Bing Lai, Bing song, Xiubi et al. Determination of three coumarins in radix glehniae from Fujian province by HPLC [J]. Modern distance education of traditional Chinese medicine in China, 18 Vol. 10, 2020. 8. Cong Jianmin, Chen Fengqing, Ye Junshuang, etc. Study on extraction technology and antibacterial activity of coumarin from Melilotus [J]. Natural product research and development, 2014, 026(004):588-593,596. 9. Huang Ting, Guo Yuhua, Ding Liyan, etc. Effect of Psoralea corylifolia L. Juice on anti-OP chemical composition [J]. Journal of Liaoning University of Traditional Chinese Medicine, 2013, 22 (05):62-64. 10. Xuelian Wang, Minmin Li, Junhua Hu, et al. Inhibitory effects of 18 coumarins on Colletotrichum gloeosporioides in Citrus [J]. Southern China fruit trees, 2013, 42(004):73-74. 11. Li Jiayan, Liu Xinxin, Ning Qing, Li Yandong, Shi Ziqi, Wei Yingjie. Efficient Identification of toxicity related components of Psoralea corylifolia based on zebrafish model [J]. Chinese herbal medicine, 2021,52(01):129-136. 12. Fan xiaulong, Chen Ran, Wu Wanqin, Liu Guoyan, Huang Kun, Jiang Feng. Determination of 20 functional components in food by liquid chromatography tandem mass spectrometry [J]. Food and machinery, 2021,37(01):86-93 98. 13. Chen, Zhi-Jing, et al. "Dietary total prenylflavonoids from the fruits of Psoralea corylifolia L. prevents age-related cognitive deficits and down-regulates Alzheimer's markers in SAMP8 mice." Molecules 23.1 (2018): 196.https://doi.org/10.3390/molecules230 14. Zhang, Yuzhu, et al. "Effects of psoralen on the pharmacokinetics of anastrozole in rats." Pharmaceutical biology 56.1 (2018): 433-439.https://doi.org/10.1080/13880209.2018.1501584 15. Chen, Xiumin, Yanfang Yang and Yingtao Zhang. "Isobavachalcone and bavachinin from Psoraleae Fructus modulate Aβ42 aggregation process through different mechanisms in vitro." Febs Letters 587.18 (2013): 2930-2935.https://doi.org/10.1016/j.febslet.2013.07. 16. Yang, Yan-Fang, Lei Zhang, and Xiu-Wei Yang. "Distribution assessments of coumarins from Angelicae Pubescentis Radix in rat cerebrospinal fluid and brain by Liquid Chromatography Tandem Mass Spectrometry analysis ." Molecules 23.1 (2018): 225.https://doi.or 17. [IF=5.192] Lin Ji et al."Psoralen, a mechanism-based inactivator of CYP2B6."Chem-Biol Interact. 2015 Oct;240:346 18. [IF=4.411] Liang Yang et al."New Insights into the Antibacterial Activity of Hydroxycoumarins against Ralstonia solanacearum."Molecules. 2016 Apr;21(4):468 19. [IF=4.411] Li Jia et al."Systematic Profiling of the Multicomponents and Authentication of Erzhi Pill by UHPLC/Q-Orbitrap-MS Oriented Rapid Polarity-Switching Data-Dependent Acquisition and Selective Monitoring of the Chemical Markers Deduced from Fingerprint Analys 20. [IF=4.379] Li Kai et al."Quantitative analysis, pharmacokinetics and metabolomics study for the comprehensive characterization of the salt-processing mechanism of Psoraleae Fructus."Sci Rep-Uk. 2019 Jan;9(1):1-10 21. [IF=4.072] Tiehua Zhang et al."Estrogenic properties of coumarins and meroterpene from the fruits of Cullen corylifolium: Experimental and computational studies."Phytochemistry. 2018 Aug;152:148 22. [IF=3.503] Yuzhu Zhang et al."Effects of psoralen on the pharmacokinetics of anastrozole in rats."Pharm Biol. 2018;56(1):433-439 23. [IF=2.675] Xiumin Chen et al."Isobavachalcone and bavachinin from Psoraleae Fructus modulate Aβ42 aggregation process through different mechanisms in vitro."Febs Lett. 2013 Sep;587(18):2930-2935 24. [IF=6.576] Li Guijie et al."Effects of Cold-Pressing and Hydrodistillation on the Active Non-volatile Components in Lemon Essential Oil and the Effects of the Resulting Oils on Aging-Related Oxidative Stress in Mice."Front Nutr. 2021 Jun;0:329 25. [IF=4.36] Yang Zhao et al."Shashen-Maidong Decoction improved chronic intermittent hypoxia-induced cognitive impairment through regulating glutamatergic signaling pathway."J Ethnopharmacol. 2021 Jun;274:114040 26. [IF=4.162] Guijie Li et al."Characterization of Oxygenated Heterocyclic Compounds and in vitro Antioxidant Activity of Pomelo Essential Oil."Drug Des Dev Ther. 2021; 15: 937-947 27. [IF=1.771] Lin Yongtao et al."Psoralen alleviates high glucose-induced HK-2 cell injury by inhibition of Smad 2 signaling via upregulation of microRNA 874."Bmc Pharmacol Toxico. 2020 Dec;21(1):1-10 |
66-97-7 - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| Overview | Psoralea corylifolia L., also known as nigroseed, broken paper, Hu Wei Zi, etc., was first recorded in the "open baby herbs". It is the legume Psoralea corylifolia L. The dry mature fruit, mainly produced in Sichuan, Henan, Shaanxi, Anhui and other places, the main chemical components of Psoralea corylifolia are pepper toxin, volatile oil, fatty oil, resin and psoralen, isopsoralen, psoralen, isopsoralidine, dihydroxyisopsoralidine, flavonoids (psoralen A, psoralen B, psoralen, new psoralen chalcone), monoterpene phenols (psoralen, etc.), coumarin. Psoralea corylifolia has the function of warming kidney, promoting Yang, promoting Qi and stopping diarrhea. Traditional Chinese medicine is used to treat impotence, enuresis, frequent micturition, cold pain of waist and knee, kidney deficiency for asthma, five more diarrhea and so on. Modern pharmacological studies have found that Psoralea corylifolia also has multiple pharmacological activities, such as anti-tumor, treatment of osteoporosis, estrogen-like effect, antibacterial and treatment of vitiligo. Psoralen, also known as psoralen, is an active ingredient extracted from plant Psoralea corylifolia, which belongs to furan coumarin. It has the effect of promoting the increase of skin melanin, and is clinically used for the treatment of vitiligo, alopecia areata and psoriasis. |
| pharmacological action | psoralen has the effect of increasing melanin. Under the irradiation of ultraviolet lamp, the phototoxic reaction can be generated, and the synthesis of DNA in epidermal cells can be selectively inhibited. |
| anticancer effect | psoralen has significant inhibitory effect on S180, Ehrlich ascites carcinoma and liver cancer H-22. Psoralen and 8-Methoxypsoralen have significant killing effect on S180 ascites cells. Both psoralen B and volatile oil have anti-cancer effects. |
| morphology of Psoralea corylifolia | Psoralea corylifolia is an annual herb, 0.5-1.5m in height, with white pilose and black-brown glandular spots. Stems were upright, branches were firm. Alternate leaves, with one lateral leaflet at the end of the branch and sometimes about 1cm in length. The leaf blade was broadly ovoid, 6-9cm in length and 5-7cm in width, the petiole was 2-4cm in length, and the lateral petioles were very short. Racemes were extracted from leaf axillae in summer, the total pedicels were very long, most of them were small flowers, with dense upper part, with head-like shape, the pedicel was short, and the Calyx was bell-shaped, flag lobe broadly obovoid; Stamens 10. Pod Oval-ovoid, about 5mm in length, black, not dehiscence at maturity. 1 seed, oblate, brown-black, attached to the Peel, with aroma. Fruit branches are picked in autumn, dried in the sun, and the fruits are rubbed out to remove impurities. Wash when used. Figure 1 extraction and separation of psoralen |
| indication | for vitiligo, psoriasis, alopecia areata, etc. Treatment of vitiligo: intramuscular injection, 2ml,1 times/d, can be used for several months. About 1h after the injection should be to the outdoor Sun 10~30min; Or with ultraviolet light distance 50cm irradiation, starting from 1~2min, daily or every other day increased by 1min, gradually increased to 10~15min. Apply the solution for external use to the affected area, starting from a small area, after a few minutes to the outdoor sun, starting from 5min, if there is no allergic reaction, can gradually increase to 20min/time; can also be irradiated with ultraviolet light, the method with intramuscular injection. Every 2~3 days to apply 1 times, adhere to a number of years or more than half a year. Large area of the patient can be intramuscular injection and external use at the same time. Treatment of psoriasis: oral, 40~80mg/Time, 2H after the whole body black light. When the projection distance was 7 ~ 17cm, the irradiation time was 15~30min. For the stubborn part of skin lesion, the distance should be short. 1 times/ (1~2) d. After the basic cure, should continue to consolidate treatment, and gradually extend the treatment time. |
| extraction | FIG. 2 extraction |
| contraindication | 1.12 children under the age of, the frail elderly and pregnant women are contraindicated. There are photosensitive diseases such as lupus erythematosus, Dermatomyositis, porphyria, polymorphic light rash, xeroderma pigmentosum and other patients disabled. Disabled in patients with severe liver disease. 4. Cataract or other lens disease patients disabled. (2015-12-28) |
| adverse reactions | the affected part may have redness, swelling and blisters after sun exposure and ultraviolet irradiation. |
| note | 1. Should wear dark glasses protection after using this product. Treatment of erythema, blisters, treatment should be suspended, after the resumption of treatment, but the sun and ultraviolet irradiation time should be shortened. 3. Injection such as precipitation of crystals, can be put in boiling water for 10 minutes, to be dissolved in the crystal and cool after use. |
| Use | has the effect of increasing skin melanin, and is suitable for vitiligo. In addition, it can be used for alopecia areata and psoriasis. phototoxic phytoalexin; When activated by UV light, psoralen induces cross-linking across strands in DNA. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:01:54
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