Sclareol - Moligand™, ≥96% , CAS No.515-03-7

CAS: 515-03-7 Cat. No.: S138935 Formula: C₂₀H₃₆O₂ Molecular Weight: 308.50 Beilstein Registry Number: 2054148 EC Number: 208-194-0

GRADE & PURITY Moligand™, ≥96%

Synonyms

1-Naphthalenepropanol, alpha-ethenyldecahydro-2-hydroxy-alpha,2,5,5,8a-pentamethyl-, (alphaR,1R,2R,4aS,8aS)-|(1R,2R,8aS)-Decahydro-1-(3-hydroxy-3-methyl-4-pentenyl)-2,5,5,8a-tetramethyl-2-naphthol|Labd-14-ene-8,13-diol, (13R)-|(1R,2R,4aS,8aS)-1-[(3R)-3-hydroxy-3-methyl-pent-4-enyl]-2,5,5,8a-tetramethyl-decalin-2-ol|1-NAPHTHALENEPROPANOL, .ALPHA.-ETHENYLDECAHYDRO-2-HYDROXY-.ALPHA.,2,5,5,8A-PENTAMETHYL-, (1R-(1.ALPHA.(R*),2.BETA.,4A.BETA.,8A.ALPHA.))-|(1R,2R,4aS,8aS)-1-[(3R)-3-hydroxy-3-methylpent-4-en-1-yl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol labd-14-ene-8,13-diol|(1R,2R,4aS,8aS)-1-((R)-3-hydroxy-3-methylpent-4-en-1-yl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol|(13R)-Labd-14-ene-8,13-diol|(1R,2R,4aS,8aS)-1-((3R)-3-hydroxy-3-methylpent-4-en-1-yl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol|1-Naphthalenepropanol, alpha-ethenyldecahydro-2-hydroxy-alpha,2,5,5,8a-pentamethyl-, (1theta-(1alpha(theta),2beta,4abeta,8aalpha))-|(1R-(1alpha(R*),2beta,4Abeta,8aalpha))-2-hydroxy-alpha,2,5,5,8a-pentamethyl-alpha-vinyldecahydronaphthalene-1-propan-1-ol|(1R,2R,4aS,8aS)-1-[(3R)-3-hydroxy-3-methylpent-4-en-1-yl]-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol|(1R,2R,4aS,8aS)-1-[(3R)-3-hydroxy-3-methylpent-4-en-1-yl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol|SCAREOL|1-NAPHTHALENEPROPANOL, alpha-ETHENYLDECAHYDRO-2-HYDROXY-alpha,2,5,5,8A-PENTAMETHYL-, (1R-(1alpha(R*),2beta,4Abeta,8Aalpha))-|SCLAREOL [INCI]|labd-14-ene-8,13-diol|(1R,2R,4aS,8aS)-1-[(3R)-3-hydroxy-3-methylpent-4-enyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol|(13R)-Labd-14-ene-8alpha,13-diol|labd-14-ene-8alpha, 13beta-diol|1-Naphthalenepropanol, alpha-ethenyldecahydro-2-hydroxy-alpha,2,5,5,8a-pentamethyl-, (alphaR,1R,2R,4aS,8aS)-: (1R,2R,4aS,8aS)-1-[(3R)-3-hydroxy-3-methylpent-4-en-1-yl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol|Sclareol (natural)|(1R,2R,4As,8aR)-1-[(3R)-3-hydroxy-3-methylpent-4-enyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol|Sclareol|(-)-SCLAREOL|1-Naphthalenepropanol, .alpha.-ethenyldecahydro-2-hydroxy-.alpha.,2,5,5,8a-pentamethyl-, (.alpha.R,1R,2R,4aS,8aS)-

Storage

Room temperature

Shipped In

Normal

Overview

Sclareol, a diterpene compound with a labdane skeleton, is mainly used as a raw material in the fragrance industry. It shows potent cytotoxic and cytostatic effect in human leukemic cell lines.

Application:

Sclareol may be used as a starting material in the synthesis of ambergris fragrance chemicals such as ambraoxide, ambrox, methylambraoxide, ambracetal, ambraketal and epiambraketal. It may also be used in the synthesis of (+)-galanolactone, (-)-8-epi-galanolactone and (+)-labdienedial.

Specifications

Synonyms

1-Naphthalenepropanol, alpha-ethenyldecahydro-2-hydroxy-alpha,2,5,5,8a-pentamethyl-, (alphaR,1R,2R,4aS,8aS)- | (1R,2R,8aS)-Decahydro-1-(3-hydroxy-3-methyl-4-pentenyl)-2,5,5,8a-tetramethyl-2-naphthol | Labd-14-ene-8,13-diol, (13R)- | (1R,2R,4aS,8aS)-1-[(3R)-3-hydroxy-3-methyl-pent-4-enyl]-2,5,5,8a-tetramethyl-decalin-2-ol | 1-NAPHTHALENEPR Show more

Specifications & Purity

Moligand™, ≥96%

Storage

Room temperature

Shipped In

Normal

Grade

Moligand™

Purity

≥96%

Names and Identifiers

Pubchem Sid

488188358

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488188358

Canonical Smiles

CC1(CCCC2(C1CCC(C2CCC(C)(C=C)O)(C)O)C)C

IUPAC Name

(1R,2R,4aS,8aS)-1-[(3R)-3-hydroxy-3-methylpent-4-enyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol

InChIKey

XVULBTBTFGYVRC-HHUCQEJWSA-N

INCHI

1S/C20H36O2/c1-7-18(4,21)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)22/h7,15-16,21-22H,1,8-14H2,2-6H3/t15-,16+,18-,19-,20+/m0/s1

Isomeric SMILES

C[C@]12CCCC([C@@H]1CC[C@@]([C@@H]2CC[C@](C)(C=C)O)(C)O)(C)C

WGK Germany

2

Molecular Weight

308.50

Beilstein

2054148

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Diterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Diterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Diterpenoids
• Alternative Parents: Tertiary alcohols Cyclic alcohols and derivatives Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Diterpenoid - Labdane diterpenoid - Tertiary alcohol - Cyclic alcohol - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Alcohol - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
• External Descriptors: Labdane and halimane diterpenoids

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)

ACHE Tclin Acetylcholinesterase (18204 Activities)

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RXRG Tclin Retinoid X receptor gamma (646 Activities)

Discover Target: RXRG

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RXRB Tclin Retinoid X receptor beta (726 Activities)

Discover Target: RXRB

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PC-3 (62116 Activities)

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SNU1 (253 Activities)

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A549 (127892 Activities)

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HCT-116 (91556 Activities)

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HUVEC (11049 Activities)

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HeLa (62764 Activities)

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PBMC (10003 Activities)

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Associated Targets(non-human)

Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Staphylococcus epidermidis (22802 Activities)

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Staphylococcus hominis (482 Activities)

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Escherichia coli (133304 Activities)

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Plasmodium falciparum (966862 Activities)

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Mus musculus (284745 Activities)

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B16 (5829 Activities)

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P388 (20296 Activities)

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RAW264.7 (28094 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Insoluble in water
• Specific Rotation[α]: -4° (C=1,CHCl3)
• Boil Point(°C): 218-220°C/19mmHg
• Melt Point(°C): 95-103 °C
• Molecular Weight: 308.500 g/mol
• XLogP3: 4.900
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 308.272 Da
• Monoisotopic Mass: 308.272 Da
• Topological Polar Surface Area: 40.500 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 429.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• 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