Basic information
- CAS
64657-18-7- Standard SMILES
C=C[C@@]1(C)CC(=O)[C@@H]2[C@@]3(C)CCCC(C)(C)[C@@H]3[C@H](O)[C@H](OC(C)=O)[C@@]2(C)O1- InChIKey
ZKZMDXUDDJYAIB-SUCLLAFCSA-N- Molecular formula
- C22H34O5
- Average molar mass
- 378.5 g/mol
- Monoisotopic mass
- 378.24062418
Overview
1,9-dideoxyforskolin is a labdane diterpenoid that is the 1,9-dideoxy derivative of forskolin. It has a role as a plant metabolite. It is an organic heterotricyclic compound, a labdane diterpenoid and an acetate ester. It is functionally related to a forskolin.
Names & identifiers
- Preferred name
- (-)-1,9-Dideoxyforskolin
- IUPAC
- [(3R,4aS,5S,6S,6aS,10aS,10bR)-3-ethenyl-6-hydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-2,5,6,6a,8,9,10,10b-octahydrobenzo[f]chromen-5-yl] acetate
- English name
- 1,9-DIDEOXYFORSKOLIN
- Molecular formula
- C22H34O5
- Molecular weight
- 378.5
Names & synonyms
1,9-DIDEOXYFORSKOLIN64657-18-7OAW710HWIXDTXSID5040384(-)-1,9-DIDEOXYFORSKOLIN[(3R,4aS,5S,6S,6aS,10aS,10bR)-3-ethenyl-6-hydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-2,5,6,6a,8,9,10,10b-octahydrobenzo[f]chromen-5-yl] acetateCHEBI:502957beta-acetoxy-8,13-epoxy-6beta-hydroxylabd-14-en-11-one(3R,4aS,5S,6S,6aS,10aS,10bR)-3-ethenyl-6-hydroxy-3,4a,7,7,10a-pentamethyl-1-oxododecahydro-1H-benzo[f]chromen-5-yl acetate(3R,4aS,5S,6S,6aS,10aS,10bR)-5-(acetyloxy)-3-ethenyldodecahydro-6-hydroxy-3,4a,7,7,10a-pentamethyl-1H-naphtho(2,1-b)pyran-1-one(3R-(3alpha,4abeta,5beta,6beta,6aalpha,10abeta,10balpha))-5-(acetyloxy)-3-ethenyldodecahydro-6-hydroxy-3,4a,7,7,10a-pentamethyl-1H-naphtho(2,1-b)pyran-1-one1H-Naphtho(2,1-b)pyran-1-one, 5-(acetyloxy)-3-ethenyldodecahydro-6-hydroxy-3,4a,7,7,10a-pentamethyl-, (3R,4aS,5S,6S,6aS,10aS,10bR)-
Show more names
ddFSKDideoxyforskolin9-DideoxyforskolinFORSKOLIN, 1,9-DIDEOXYDIDEOXYFORSKOLIN, 1,9-Dideoxyforskolin from Coleus forskohlii
Properties
Computed structural properties
- XLogP
- 3.3
- Topological polar surface area
- 72.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 3
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 670
Experimental & physicochemical properties
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C20 isoprenoids (diterpenes) [PR0104]
Physicochemical properties
- Melting point
- 149 · 149-150℃
- Boiling point
- 455.003 · 455.003±45.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.125 · 1.125±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- storage temp.
- 20 °C · −20°C
- solubility
- 28 mg/mL · methanol: 28 mg/mL
- form
- solid
- pka
- 13.757 · 13.757±0.70(predicted)
- color
- white
- optical activity
- 26 · [α]26/D +93.6°, c = 6.12 in chloroform(lit.)
- InChI
- 1S/C22H34O5/c1-8-20(5)12-14(24)16-21(6)11-9-10-19(3,4)17(21)15(25)18(26-13(2)23)22(16,7)27-20/h8,15-18,25H,1,9-12H2,2-7H3/t15-,16,17-,18-,20-,21+,22-/m0/s1
- InChIKey
- ZKZMDXUDDJYAIB-OJPJTMFRSA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
P280, P302+P352, P317, P321, P362+P364, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H312
- Precautionary statements
- P280-P302+P352-P312-P322-P363-P501
Chemistry & industry
Applications
DescriptionForskolin is a naturally-occurring diterpene that activates adenylyl cyclase through its catalytic subunit and is commonly used to raise levels of cAMP in a wide variety of intact cells and tissue preparations. 1,9-dideoxy Forskolin is an analog of forskolin that interacts with, but does not activate, adenylyl cyclase.
Uses1,9-Dideoxyforkskolin does not activate adenylyl cyclase and is an inactive analog of Forskolin (F701800), a diterpene isolated from Coleus forskohlii, possessing vasodilating and cardiostimulatory properties. Forskolin resensitizes cell receptors by activating the enzyme adenylyl cyclase and increasing the intracellular levels of cAMP.
Suppliers16 total
上海纽雀客生物科技有限公司13916276291 · [email protected]
Aladdin Scientific[email protected]
Syntechem Co.,Ltd[email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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