| Identification | Back Directory | [Name]
Rosmanol | [CAS]
80225-53-2 | [Synonyms]
ROSMARINIC ACID
20-Deoxocarnosol
rat tail oxalic acid
Keywords honeysuckle extract
6β,7α,11,12-Tetrahydroxyabieta-8,11,13-trien-20-oic acid 20,6-lactone
(4bR,8aS,9S,10S)-3,4,10-Trihydroxy-2-isopropyl-8,8-dimethyl-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epoxymethano)phenanthren-12-one
(4bR,8aS,9R,10S)-3,4,10-trihydroxy-2-isopropyl-8,8-dimethyl-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epoxymethano)phenanthren-12-one
(4aR,10aα)-1,3,4,9,10,10a-Hexahydro-5,6,9α-trihydroxy-1,1-dimethyl-7-(1-methylethyl)-2H-10β,4aβ-(epoxymethano)phenanthren-12-one
2H-10,4a-(Epoxymethano)phenanthren-12-one, 1,3,4,9,10,10a-hexahydro-5,6,9-trihydroxy-1,1-dimethyl-7-(1-methylethyl)-, (4aR,9S,10S,10aS)-
[4aR-(4aa,9b,10a,10ab)]-1,3,4,9,10,10a-Hexahydro-5,6,9-trihydroxy-1,1-dimethyl-7-(1-methylethyl)-2H-10,4a-(epoxymethano)phenanthren-12-one | [Molecular Formula]
C20H26O5 | [MDL Number]
MFCD12031636 | [MOL File]
80225-53-2.mol | [Molecular Weight]
346.42 |
| Chemical Properties | Back Directory | [Melting point ]
212-213 °C(Solv: ethyl ether (60-29-7)) | [Boiling point ]
574.2±50.0 °C(Predicted) | [density ]
1.33 | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
DMSO: soluble | [form ]
A solid | [pka]
9.07±0.60(Predicted) | [color ]
White to off-white | [Major Application]
food and beverages | [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 |
| Hazard Information | Back Directory | [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) |
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