Rosmanol Chemical Properties

Melting point:

212-213 °C(Solv: ethyl ether (60-29-7))

Boiling point:

574.2±50.0 °C(Predicted)

Density 

1.33

storage temp. 

2-8°C

solubility 

DMSO: soluble

form 

A solid

pka

9.07±0.60(Predicted)

color 

White to off-white

InChI

InChI=1S/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

InChIKey

LCAZOMIGFDQMNC-FORWCCJISA-N

SMILES

C1(C)(C)[C@@]2([H])[C@]3(C(=O)O[C@]2([H])[C@@H](O)C2=C3C(O)=C(O)C(C(C)C)=C2)CCC1

Rosmanol Usage And Synthesis

Uses

food and beverages

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)

Rosmanol(80225-53-2)Related Product Information

• Ethyl 2-(Chlorosulfonyl)acetate
• Glycine
• Rosemary oil
• Citric acid
• Rosmarinic acid
• Cryptotanshinone
• Rosemary Herb Extract
• Luteolin
• Salidroside
• Baicalin
• DL-Limonene
• SAGE OIL, SPANISH
• Caffeine
• Folic acid
• Ascoric Acid
• Rosemary
• Rosmanol
• phosphoric acid