CAS 15358-48-2

13-hydroxylupanine

Description:

13-Hydroxylupanine is a chemical compound classified as a triterpenoid, specifically a type of lupane derivative. It is characterized by the presence of a hydroxyl group (-OH) at the 13th carbon position of the lupane skeleton, which contributes to its unique chemical properties and biological activities. This compound is typically found in various plant species and is of interest in the field of natural products chemistry due to its potential pharmacological effects. Triterpenoids like 13-hydroxylupanine are known for their diverse biological activities, including anti-inflammatory, antioxidant, and anticancer properties. The molecular structure of 13-hydroxylupanine allows for interactions with biological systems, making it a subject of research in medicinal chemistry. Additionally, its solubility and stability can vary depending on environmental conditions, which may influence its bioavailability and efficacy in therapeutic applications. Overall, 13-hydroxylupanine represents a significant area of study for its potential health benefits and applications in drug development.

Formula: C₁₅H₂₄N₂O₂

InChI: InChI=1/C15H24N2O2/c18-12-4-5-16-8-10-6-11(14(16)7-12)9-17-13(10)2-1-3-15(17)19/h10-14,18H,1-9H2/t10-,11-,12+,13-,14-/m1/s1

InChI key: InChIKey=JVYKIBAJVKEZSQ-YHQUGGNUSA-N

SMILES: O[C@@H]1C[C@]2([C@]3(C[C@@](CN2CC1)([C@@]4(N(C3)C(=O)CCC4)[H])[H])[H])[H]

Synonyms:

• (+)-13α-Hydroxylupanine
• (13Beta)-13-Hydroxyspartein-2-One
• (2S,7S,7aR,14S,14aS)-Dodecahydro-2-hydroxy-7,14-methano-2H,11H-dipyrido[1,2-a:1′,2′-e][1,5]diazocin-11-one
• (6Beta,7Alpha,9Alpha,13Alpha)-13-Hydroxyspartein-2-One
• (9Alpha,13Beta)-13-Hydroxyspartein-2-One
• 13-Hydroxylupanin
• 13-Hydroxyspartein-2-One
• 13-Oxylupanine
• 13α-Hydroxy-2-oxosparteine
• 7,14-Methano-2H,11H-dipyrido(1,2-a:1',2'-e)(1,5)diazocin-11-one, dodecahydro-2-hydroxy-, (2S-(2alpha,7beta,7abeta,14beta,14aalpha))-
• 7,14-Methano-2H,11H-dipyrido[1,2-a:1′,2′-e][1,5]diazocin-11-one, dodecahydro-2-hydroxy-, (2S,7S,7aR,14S,14aS)-
• 7,14-Methano-2H,11H-dipyrido[1,2-a:1′,2′-e][1,5]diazocin-11-one, dodecahydro-2-hydroxy-, [2S-(2α,7β,7aβ,14β,14aα)]-
• 7,14-Methano-4H,6H-dipyrido(1,2-a:1',2'-e)(1,5)diazocin-4-one, dodecahydro-9-hydroxy-, (7S-(7alpha,7abeta,9beta,14alpha,14aalpha))- (9CI)
• 7,14-Methano-4H,6H-dipyrido[1,2-a:1′,2′-e][1,5]diazocin-4-one, dodecahydro-9-hydroxy-, [7S-(7α,7aβ,9β,14α,14aα)]-
• Alkaloid C 2, from Cadia purpurea
• Brn 0087896
• Dodecahydro-2-hydroxy-7,14-methano-2H,11H-dipyrido(1,2-a:1',2'-e)(1,5)diazocin-11-one (2S-(2alpha,7beta,7abeta,14beta,14aalpha))-
• Hydroxylupanin
• Hydroxylupanine
• Jamaidine
• Lupanine, 13-Hydroxy-
• Lupanine, 13-alpha-hydroxy-
• Lupanine, 13alpha-hydroxy- (8CI)
• Lupanine, 13α-hydroxy-
• Lupanine, hydroxy-
• Lupanine, hydroxy- (6CI)
• Luparine, hydroxy-
• Nsc 70827
• Oxylupanine
• d-Hydroxylupanine
• (+)-13-Hydroxylupanine
• 13-Hydroxylupanine
• 4-25-00-00082 (Beilstein Handbook Reference)
• 7,14-Methano-2H,11H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-11-one, dodecahydro-2-hydroxy-, (2S,7S,7aR,14S,14aS)-
• (7S,7aβ,9β,14S,14aα)-Dodecahydro-9-hydroxy-7,14-methano-4H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-4-one

13-Hydroxylupanine

CAS: 15358-48-2

Formula: C₁₅H₂₄N₂O₂

Purity: 97.0%

Color and Shape: Solid

Molecular weight: 264.3633

Ref: IN-DA00ASI0

13-Hydroxylupanine

CAS: 15358-48-2

13-Hydroxylupanine is a natural product from Cytisus scoparius.

Formula: C₁₅H₂₄N₂O₂

Purity: 98%

Color and Shape: Solid

Molecular weight: 264.36

Ref: TM-TN6574

13-Hydroxy Lupanine

CAS: 15358-48-2

Formula: C₁₅H₂₄N₂O₂

Molecular weight: 264.37

Ref: 4Z-L-127001

13-hydroxylupanine

CAS: 15358-48-2

Natural alkaloid

Formula: C₁₅H₂₄N₂O₂

Purity: ≥ 90.0 % (HPLC)

Color and Shape: Powder

Molecular weight: 264.36

Ref: 5G-86290

(+)-13α-Hydroxylupanine

CAS: 15358-48-2

Applications (+)-13α-Hydroxylupanine is used in analytical studies for the determination of Lupinus polyphyllus by thin-layer chromatography and fluorescence.
References Karlsson, E.M., et al.: J. Chromat., 155, 218 (1978);

Formula: C₁₅H₂₄N₂O₂

Color and Shape: Off-White To Light Yellow

Molecular weight: 264.36

Ref: TR-H943795

(+)-13α-Hydroxylupanine

CAS: 15358-48-2

(+)-13α-Hydroxylupanine is a quinolizidine alkaloid that has been shown to have an inhibitory effect on the production of melatonin in the brain by binding to melatonin receptors. Melatonin is produced in the pineal gland and regulates sleep-wake cycles. It has also been shown to be a potent inhibitor of cellular uptake, which may explain its use as a model system for studying uptake kinetics. This compound has been found to be present in plants such as Datura stramonium and Datura innoxia. (+)-13α-Hydroxylupanine is also used for cell culture studies, where it inhibits cell growth and induces apoptosis.

Formula: C₁₅H₂₄N₂O₂

Purity: Min. 95%

Molecular weight: 264.36 g/mol

Ref: 3D-QAA35848