80225-53-2 Usage
Anticancer Research
This is a polyphenol and an ester of caffeic acid and 3,4-dihydroxyphylllique acid.This is commonly found in Boraginaceae species and Nepettoideae, a Lamiaceaesubfamily. It plays an important role in anti-inflammatory, antitumor, andantiproliferation activities. It shows a dose-dependent inhibition of invasion,migration, and adhesion of LS-174-T human colon carcinoma cells. It inhibits thebone metastasis from breast cancer via NF-κB and its downward IL-8 pathway(Wang et al. 2012). It reduces ERK and COX-2 phosphorylation in colon carcinoma.It reduces the activity of DNA methyltransferase and interferes with RANKL/RANK/OPG networks in breast cancer cells. It targets NF-kB pathway in U938cells and PKA/CREB/MITF pathways in melanoma cells (Singh et al. 2016b). InU938 human leukemic cells, it sensitizes TNF-α-induced apoptosis by affectingNF-kB and ROS and inhibits the activation of NF-kB by inhibiting IκBαphosphorylation and degradation. It also reduces the levels of promoter activity ofCOX-2 protein induced by TPA in HT-29 colon cancer cells and antagonizes TPAstimulating effects on COX-2 expression (Petersen and Simmonds 2003).
Cytotoxicity
IC50 (μg/mL): 1.71 (A2780), 6.96(SW1573), 10.13 (WiDr), 10.13 (T-47D),1.46 (HBL-100) (Guerrero et al. 2006;Zhang et al. 2017)
Check Digit Verification of cas no
The CAS Registry Mumber 80225-53-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,0,2,2 and 5 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 80225-53:
(7*8)+(6*0)+(5*2)+(4*2)+(3*5)+(2*5)+(1*3)=102
102 % 10 = 2
So 80225-53-2 is a valid CAS Registry Number.
InChI:InChI=1/C20H26O5/c1-9(2)10-8-11-12(15(23)13(10)21)20-7-5-6-19(3,4)17(20)16(14(11)22)25-18(20)24/h8-9,14,16-17,21-23H,5-7H2,1-4H3/t14-,16+,17-,20-/m0/s1
80225-53-2Relevant articles and documents
Semisynthesis and biological evaluation of abietane-type diterpenes. Revision of the structure of rosmaquinone
Marrero, Joaquin G.,Moujir, Laila,Andres, Lucia S.,Montano, Nayely P.,Araujo, Liliana,Luis, Javier G.
scheme or table, p. 1385 - 1389 (2010/03/26)
The new aromatic diterpenes 7β-O-benzylrosmanol (3), 7β-O-benzyl-11,12-di-O-methylrosmanol (4), and 7α-thiophenylcarnosic acid (5) have been obtained by partial synthesis from carnosol (1), an abundant natural diterpene present in Salvia species. The stru
Semisynthesis of rosmanol and its derivatives. Easy access to abietatriene diterpenes isolated from the genus Salvia with biological activities
Marrero, Joaquin G.,Andres, Lucia S.,Luis, Javier G.
, p. 986 - 989 (2007/10/03)
The known diterpenes rosmanoi (3), rosmaquinone (4), 7-methoxyrosmanol (5), 7-ethoxyrosmanol (6), galdosol (7), and epirosmanol (8) have been obtained by partial synthesis from carnosol (2), an abundant natural product present in Salvia species. The physical and spectroscopic data of these semisynthetic diterpenes were identical to those of authentic natural samples and with data reported in the literature. These abietane diterpenes have very interesting biological activities and are present in the genus Salvia in low quantities; thus, the semisynthetic approach described here represents an efficient alternative method to obtain these compounds. Additionally, the known diterpene 16-hydroxyrosmanol (10) and a new aromatic diterpene 11 were obtained from 16-hydroxycarnosol (9) by reaction with Ph3P/NBS in CH2Cl2. The structure of the new compound 11 was established from its spectroscopic data as 12,16-epoxycarnosol.
