ChemicalBook > CAS DataBase List > (4aS,10aS)-6-hydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahy dro-2H-phenanthren-9-one

(4aS,10aS)-6-hydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahy dro-2H-phenanthren-9-one

Product Name
(4aS,10aS)-6-hydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahy dro-2H-phenanthren-9-one
CAS No.
511-05-7
Chemical Name
(4aS,10aS)-6-hydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahy dro-2H-phenanthren-9-one
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)-
CBNumber
CB11254043
Molecular Formula
C20H28O2
Formula Weight
300.44
MOL File
511-05-7.mol
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(4aS,10aS)-6-hydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahy dro-2H-phenanthren-9-one Property

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)
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Arctom
Product number
CFN92187
Product name
Sugiol
Packaging
5mg
Price
$510
Updated
2021/12/16
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(4aS,10aS)-6-hydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahy dro-2H-phenanthren-9-one Chemical Properties,Usage,Production

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

(4aS,10aS)-6-hydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahy dro-2H-phenanthren-9-one Preparation Products And Raw materials

Raw materials

Preparation Products

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511-05-7, (4aS,10aS)-6-hydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahy dro-2H-phenanthren-9-oneRelated Search:


  • (4aS,10aS)-6-hydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahy dro-2H-phenanthren-9-one
  • (+)-Sugiol
  • (4aS)-2,3,4,4a,10,10aα-Hexahydro-6-hydroxy-1,1,4a-trimethyl-7-isopropylphenanthren-9(1H)-one
  • 12-Hydroxyabieta-8,11,13-triene-7-one
  • Sugiol
  • 10-Deoxoxanthoperol
  • 9(1H)-Phenanthrenone, 2,3,4,4a,10,10a-hexahydro-6-hydroxy-1,1,4a-trimethyl-7-(1-methylethyl)-, (4aS,10aS)-
  • 511-05-7