Kahweol - ≥97% , CAS No.6894-43-5

CAS: 6894-43-5 Cat. No.: K274796 Molecular Weight: 314.42

GRADE & PURITY ≥97%

Synonyms

7-(Hydroxymethyl)-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b-decahydro-5a,8-methanocyclohepta[5,6]naphtho[2,1-b]furan-7-ol | (3bS,5aS,7R,8R,10aR,10bS)-3b,4,5,6,7,8,9,10,10a,10b-Decahydro-7-hydroxy-10b-methyl-5a,8-methano-5aH-cyclohepta[5,6]naphtho[2,1-b]furan-7

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Store at -20°C. Store under desiccating conditions. The product can be stored for up to 12 months.

Specifications

Synonyms

7-(Hydroxymethyl)-10b-methyl-3b, 4, 5, 6, 7, 8, 9, 10, 10a, 10b-decahydro-5a, 8-methanocyclohepta[5, 6]naphtho[2, 1-b]furan-7-ol | (3bS, 5aS, 7R, 8R, 10aR, 10bS)-3b, 4, 5, 6, 7, 8, 9, 10, 10a, 10b-Decahydro-7-hydroxy-10b-methyl-5a, 8-methano-5aH-cyclohepta[5, 6]naphtho[2, 1-b]furan-7

Specifications & Purity

≥97%

Biochemical and Physiological Mechanisms

Diterpene molecule found in coffee beans. Increases glutathione S-transferase activity in the gut mucosa of mice and, with the diterpene cafestol, induces glutathione S-transferase expression in rat livers. Displays anti-inflammatory effects in RAW macrop

Storage

Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

ACTIVATOR

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥97%

Names and Identifiers

• Pubchem Sid: 488187514
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488187514
• Canonical Smiles: CC12C=CC3=C(C1CCC45C2CCC(C4)C(C5)(CO)O)C=CO3
• IUPAC Name: (1S,4S,12S,13R,16R,17R)-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadeca-5(9),6,10-trien-17-ol
• InChIKey: JEKMKNDURXDJAD-HWUKTEKMSA-N
• INCHI: 1S/C20H26O3/c1-18-7-5-16-14(6-9-23-16)15(18)4-8-19-10-13(2-3-17(18)19)20(22,11-19)12-21/h5-7,9,13,15,17,21-22H,2-4,8,10-12H2,1H3/t13-,15-,17+,18-,19+,20+/m1/s1
• Isomeric SMILES: C[C@@]12C=CC3=C([C@H]1CC[C@]45[C@H]2CC[C@H](C4)[C@](C5)(CO)O)C=CO3
• Molecular Weight: 314.42
• Reaxy-Rn: 293653
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=293653&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Naphthofurans

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Naphthofurans
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Naphthofurans
• Alternative Parents: Tertiary alcohols Heteroaromatic compounds Furans Cyclic alcohols and derivatives 1,2-diols Oxacyclic compounds Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Naphthofuran - Heteroaromatic compound - Tertiary alcohol - Furan - Cyclic alcohol - 1,2-diol - Oxacycle - Organic oxygen compound - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Alcohol - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as naphthofurans. These are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

VDR Tclin Vitamin D receptor (26531 Activities)

Discover Target: VDR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

Discover Target: MEN1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO
• Molecular Weight: 314.400 g/mol
• XLogP3: 3.400
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 314.188 Da
• Monoisotopic Mass: 314.188 Da
• Topological Polar Surface Area: 53.600 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 545.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 6
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Wenjiang Dong, Qiyu Chen, Changqing Wei, Rongsuo Hu, Yuzhou Long, Ying Zong, Zhong Chu.  (2021)  Comparison of the effect of extraction methods on the quality of green coffee oil from Arabica coffee beans: Lipid yield, fatty acid composition, bioactive components, and antioxidant activity.  ULTRASONICS SONOCHEMISTRY,      [PMID:33965776] [10.1016/j.ultsonch.2021.105578]

2. Qiyu Chen, Wenjiang Dong, Changqing Wei, Rongsuo Hu, Yuzhou Long.  (2020)  Combining integrated ultrasonic-microwave technique with ethanol to maximise extraction of green coffee oil from Arabica coffee beans.  INDUSTRIAL CROPS AND PRODUCTS,      [PMID:] [10.1016/j.indcrop.2020.112405]