| Identification | Back Directory | [Name]
(4aS,10aS)-6-hydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahy dro-2H-phenanthren-9-one | [CAS]
511-05-7 | [Synonyms]
Sugiol
(+)-Sugiol
10-Deoxoxanthoperol
12-Hydroxyabieta-8,11,13-triene-7-one
(4aS)-2,3,4,4a,10,10aα-Hexahydro-6-hydroxy-1,1,4a-trimethyl-7-isopropylphenanthren-9(1H)-one
(4aS,10aS)-6-hydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahy dro-2H-phenanthren-9-one
9(1H)-Phenanthrenone, 2,3,4,4a,10,10a-hexahydro-6-hydroxy-1,1,4a-trimethyl-7-(1-methylethyl)-, (4aS,10aS)- | [Molecular Formula]
C20H28O2 | [MOL File]
511-05-7.mol | [Molecular Weight]
300.44 |
| Chemical Properties | Back Directory | [Melting point ]
290-292 °C (decomp) | [Boiling point ]
185-205 °C(Press: 0.1 Torr) | [density ]
1.049±0.06 g/cm3(Predicted) | [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Powder | [pka]
8.71±0.60(Predicted) | [color ]
White to off-white | [LogP]
6.770 (est) |
| Hazard Information | Back Directory | [Uses]
Sugiol is an abietane diterpenoid, can be isolated from Calocedrus formosana bark. Sugiol has anti-inflammatory activity, could effectively reduce intracellular reactive oxygen species (ROS) production in lipopolysaccharide (LPS)-stimulated macrophages[1]. | [Definition]
ChEBI: Sugiol is an abietane diterpenoid that is ferruginol in which the methylene group para to the phenolic hydroxy group has been substituted by an oxo group. It has a role as a plant metabolite, an antiviral agent, an antineoplastic agent, an antioxidant and a radical scavenger. It is an abietane diterpenoid, a carbotricyclic compound, a meroterpenoid, a member of phenols and a cyclic terpene ketone. It is functionally related to a ferruginol. | [Cytotoxicity]
IC50 (μg/mL): <50 (SW620, HCT116,MDA-MB-231, NCI-H23, and A549)(Son et al. 2005)
IC50 (μg/mL): >30.04 (MRC-5, PC-3),23.98 (A549), 20.62 (Hl-60), 26.4(PANC-1), 10.82 (BxPC-3) (Li et al.2013). | [target]
ROS | IL Receptor | TNF-α | MAPK | ERK | JNK | p38MAPK | [IC 50]
ERK1; ERK2; p38 MAPK; JNK1; JNK2; IL-1β | [References]
[1] Chao KP, et al. Anti-inflammatory activity of sugiol, a diterpene isolated from Calocedrus formosana bark. Planta Med. 2005 Apr;71(4):300-5. DOI:10.1055/s-2005-864094 |
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