(5Z,9Z,13E)-Geranylgeranylacetone
Basic information
- CAS
6809-52-5- Standard SMILES
CC(=O)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C- InChIKey
HUCXKZBETONXFO-UHFFFAOYSA-N- Molecular formula
- C23H38O
- Average molar mass
- 330.5 g/mol
- Monoisotopic mass
- 330.29226583
Names & identifiers
- Preferred name
- (5Z,9Z,13E)-Geranylgeranylacetone
- IUPAC
- 6,10,14,18-tetramethylnonadeca-5,9,13,17-tetraen-2-one
- English name
- Teprenone
- Molecular formula
- C23H38O
- Molecular weight
- 330.55
Names & synonyms
6,10,14,18-tetramethylnonadeca-5,9,13,17-tetraen-2-one(5Z,9Z,13E)-GeranylgeranylacetoneC23H38O(5Z,9Z,13Z)-GeranylgeranylacetoneMFCD00869547SCHEMBL157511orb1302201CHEMBL4288428DTXSID50859989HUCXKZBETONXFO-UHFFFAOYSA-NDAA87924s5006
Show more names
Teprenone RSgeranylgeranylacetoneSelbexeprenoneTEPRENONETeprononeUNII-S8S8451A4OTeprenone, >=98%TetraprenylacetoneAll trans-Teprenone
NS000364076,10,14,18-tetramethyl-5,9,13,17-nonadecatetraene-2-on
Database identifiers
- CAS
6809-52-5- PubChem CID
- 5399
- DTXSID
DTXSID50859989- ChEMBL
CHEMBL4288428
Properties
Computed structural properties
- XLogP
- 7.4
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 12
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 482
Physicochemical properties
- Boiling point
- 0.01 · bp0.01 155-160°
- Density
- 420.5 · d420.5 0.9081
- refractive index
- 20 · nD20 1.4947
- storage temp.
- -20 °C · -20°C
- solubility
- 5 mg/mL · DMSO: >5mg/mL
- form
- liquid
- color
- clear
- Merck
- 14 · 14,9228
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
- Cosmetics Ingredients Functions
- SKIN CONDITIONING
- InChI
- InChI=1S/C23H38O/c1-19(2)11-7-12-20(3)13-8-14-21(4)15-9-16-22(5)17-10-18-23(6)24/h11,13,15,17H,7-10,12,14,16,18H2,1-6H3
- InChIKey
- SBOCYPUKNYDTSX-DMLVRTFPSA-N
- SMILES
- CC(=O)CCC=C(C)CCC=C(C)CCC=C(C)CC/C=C(/C)\C
- LogP
- 8.2 · 8.200 (est)
- CAS DataBase Reference
- 6809 · 6809-52-5(CAS DataBase Reference)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- rtecs
- RA5391300
- hs_code
- 2914.19.0000
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
DescriptionTeprenone (geranylgeranylacetone) is an antiulcer agent whose synthesis was inspired by the gastric protecting properties of Coenzyme Q10. Teprenone is reported to act via enhancement of gastric mucosal glycoprotein secretion.
DescriptionGeranylgeranylacetone is an inducer of heat shock protein (Hsp) expression that has been shown to increase Hsp70 (also known as Hsp72 and HspA1A), Hsp22 (HspB8), Hsp27 (HspB1), Hsp90 (HspC), and Hsp105 (HspH1) levels in various cells and tissues. It is orally bioavailable and has diverse effects in vivo, including hepatoprotective, neuroprotective, and antiulcerative effects. The effects of geranylgeranylacetone on Hsp expression are more pronounced under stress conditions.
UsesAn anti-ulcerative. Geranylgeranylacetone can induce expression of HSP70, HSPB8, and HSPB1. Induction of HSP70 expression is protective against the development of various diseases, such as inflammatory bowel disease, hypoxic/ischemic brain injury and spinal and bulbar muscular atrophy (cytoprotective and anti-inflammatory effects). Reports indicate that GGA protects against NSAID-induced gastric and intestinal lesions by induction of HSP70 expression. Other studies have shown that GGA induces expression of HSPB8 and HSPB1 and reduces the formation of amyloid oligomers as well as insoluble aggregates in HSPB5 R120G TG mice.
UsesGeranylgeranylacetone has been used as an inducer of heat shock protein 70 (HSP70) to analyze its protective effects against cerebral ischemia/reperfusion (I/R).
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