481-34-5

Basic information

• Product Name: α-cadinol
• Synonyms: α-cadinol;ALPHACADINOL;1,2,3,4,4a,7,8,8a-Octahydro-1,4,4,6-tetramethyl-1-naphthol;(1R)-1,2,3,4,4aβ,7,8,8aα-Octahydro-1,6-dimethyl-4β-isopropyl-1-naphthol;1-α-Cadinol
• CAS NO: 481-34-5
• Molecular Formula: C₁₅H₂₆O
• Molecular Weight: 222.37
• Mol File: 481-34-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 137.5-138.5 °C
• Boiling Point: 303.393°C at 760 mmHg
• Flash Point: 128.315°C
• Appearance: /
• Density: 0.937g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.49
• PKA: 15.05±0.60(Predicted)
• CAS DataBase Reference: α-cadinol(CAS DataBase Reference)
• NIST Chemistry Reference: α-cadinol(481-34-5)
• EPA Substance Registry System: α-cadinol(481-34-5)

Safety Data

• Hazardous Substances Data: 481-34-5(Hazardous Substances Data)

Usage

General Description

α-cadinol is a sesquiterpene alcohol, commonly found in the essential oils of plants such as magnolia, rosewood, and ylang-ylang. It is characterized by its woody, floral, and slightly spicy aroma. α-cadinol has been studied for its potential therapeutic properties, including its anti-inflammatory, antimicrobial, and analgesic effects. α-cadinol has also shown promise as a natural insecticide and repellent. In addition, research has suggested that this chemical may have potential applications in the pharmaceutical and cosmetic industries due to its diverse range of biological activities. Overall, α-cadinol holds promise as a valuable natural compound with various potential applications in different industries.

InChI:InChI=1/C15H26O/c1-10(2)12-7-8-15(4,16)14-6-5-11(3)9-13(12)14/h9-10,12-14,16H,5-8H2,1-4H3/t12-,13-,14+,15+/m0/s1

Upstream product

• 64-18-6 formic acid 
• 74841-87-5 (-)-germacra-1(10),5(E)-dien-4β-ol 
• 74799-64-7 α-cadinol formate 
• 372-97-4 farnesyl pyrophosphate 
• 14912-44-8 (+)-α-Ylangene 
• 74799-64-7 T-cadinol formate 
• 94853-23-3 C₂₂H₃₄N₂O₃S 
• 80873-83-2 1-(2-Diethylaminoethoxy)-4-isopropyl-cyclohexadien-1,4 
• 94853-18-6 rac-(1R,2S,5R,6R)-2-Hydroxy-5-isopropyl-2-methyl-bicyclo<4.4.0>decan-7-on 
• 94853-13-1 rac-(1R,2S,5R,6S,7R)-7-Isopropenyl-5-isopropyl-2-methyl-bicyclo<4.4.0>decan-2-ol 
• 2543-74-0 rac-(1R,2S,5R,6R,8R)-2-Hydroxy-5-isopropyl-2,8-dimethyl-bicyclo<4.4.0>decan-7-on 
• 94853-14-2 rac-(1R,2S,5R,6R,7R)-(2-Hydroxy-5-isopropyl-2-methyl-bicyclo<4.4.0>dec-7-yl)-methyl keton 
• 94853-21-1 rac-(1R,2S,5R,6R,7R)-5-Isopropyl-2-methyl-2-(1,3,6-trioxaheptyl)-bicyclo<4.4.0>decan-7-ol 
• 94853-12-0 rac-(1R,5R,6S,7R)-7-Isopropenyl-5-isopropyl-bicyclo<4.4.0>decan-2-on 

Downstream Products

• 16641-30-8 4,10-dichloro-4βH,10βH-cadinane 
• 65648-26-2 α-cadinol p-nitrobenzoate 
• 29259-92-5 (1S,4aS,5S,8R,8aR)-8-Isopropyl-2,5-dimethyl-decahydro-naphthalene-1,2,5-triol 
• 483-74-9 (-)-γ-cadinene 
• 19435-97-3 δ-cadinol 
• 35124-30-2 Amorphan-4α.9β-diol 
• 101106-71-2 5,6-Epoxy-4-isopropyl-1,6-dimethyl-decahydro-[1]naphthol 
• 483-78-3 cadalene 
• 20085-91-0 (1R,6R,7S,10R)-10-hydroxy-4⁽⁵⁾-cadinen-3-one 
• 398147-34-7 15-hydroxy-α-cadinol 
• 35049-27-5 (+/-)-Oplopanone 
• 35124-31-3 Amorphan-4-on-9β-ol 
• 35124-32-4 Cadinan-4-on-9β-ol 

Relevant articles and documents

Antimalarial Properties of Simplified Kalihinol Analogues

Several kalihinol natural products, members of the broader isocyanoterpene family of antimalarial agents, are potent inhibitors of Plasmodium falciparum, the agent of the most severe form of human malaria. Our previous total synthesis of kalihinol B provided a blueprint to generate many analogues within this family, some as complex as the natural product and some much simplified and easier to access. Each analogue was tested for blood-stage antimalarial activity using both drug-sensitive and -resistant P. falciparum strains. Many considerably simpler analogues of the kalihinols retained potent activity, as did a compound with a different decalin scaffold made in only three steps from sclareolide. Finally, one representative compound showed reasonable stability toward microsomal metabolism, suggesting that the isonitrile functional group that is critical for activity is not an inherent liability in these compounds.

Stereochemistry of 1,6-germacradien-5-ol, a constituent of the needles of Scots pine (Pinus sylvestris) and of the defence secretion from larvae of the pine sawfly Neodiprion sertifer

(-)-1,6-Germacradien-5-ol [(E,E)-1,5-dimethyl-8-isopropylcyclodeca-1,6-dien-5-ol, 1] has been isolated from the defence secretion from larvae of the pine sawfly Neodiprion sertifer and from needles of Scots pine (Pinus sylvestris). It was characterized by means of spectroscopic methods and by its optical rotation. Acid-promoted transannular cyclisation isomerised 1 to the known (-)-α-cadinol (4), whereby the configuration at position 8 was established as S. The configuration at the second stereocentre, position 5, carrying the alcohol group is discussed on the basis of molecular mechanics calculations (MM2), NMR shift values, coupling constants and NOESY experiments. 1-endo-Bourbonanol (7a) and (-)-5-methoxy-1,6-germacradiene (8) were prepared from 1 and investigated by NMR spectroscopy. The evidence collected indicated that the stereoisomer isolated was (5S,8S)-1,6-germacradien-5-ol.

STEREOSELEKTIVE TOTALSYNTHESE VON (+/-)-TORREYOL

Enones of formulae Ia-d undergo cyclization to give stereoselectively the enol esters IIa-d, respectively.IIa-d are suitable synthones for some sesquiterpene syntheses.-In this paper the synthesis of torreyol (1) is described by an all step strereocontrolled reaction sequence: cyclization educt 10 (Ic) was prepared by alkylation of 8 with 5 and enol ether cleavage of 9.The reaction sequence 11a (IIc)14a 1518 (ester hydrolysis, formation of the tert. alcohol, degradation of the isopropenyl group) followed by oxidation resulted in the formation of ketone 19 whose relative configuration was determined by the 2D J-resolved 400 MHz (1)H NMR spectrum.After methylation at C-8 (2223) the tosylhydrazone 25 underwent Bamford-Stevens reaction to yield (+/-)-1.