Labda-8(20),14-dien-13-ol, (13R)-
Basic information
- CAS
596-85-0- Standard SMILES
C=CC(C)(O)CC[C@H]1C(=C)CC[C@H]2C(C)(C)CCC[C@]12C- InChIKey
CECREIRZLPLYDM-OQLBXJDTSA-N- Molecular formula
- C20H34O
- Average molar mass
- 290.5 g/mol
- Monoisotopic mass
- 290.2609657
Overview
Labda-8(20),14-dien-13-ol, (13R)- has been reported in Murraya paniculata, Murraya exotica, and Vitex agnus-castus with data available.
Names & identifiers
- Preferred name
- Labda-8(20),14-dien-13-ol, (13R)-
- IUPAC
- 5-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-1-en-3-ol
- English name
- MANOOL
- Molecular formula
- C20H34O
- Molecular weight
- 290.48
Names & synonyms
Labda-8(20),14-dien-13-ol, (13R)-(+)-manoolNSC 165961NSC 666751UNII-AT5PJ0PV00SCHEMBL183717315-(5,5,8a-Trimethyl-2-methylenedecahydro-1-naphthalenyl)-3-methyl-1-penten-3-ol #1-Naphthalenepropanol, alpha-ethenyldecahydro-alpha,5,5,8a-tetramethyl-2-methylene-, (1S-(1alpha(S*),4abeta,8aalpha))-DA-648404aR-trans-5-(1,5,5,8aS-Tetramethyl-2-methylenedecahydro-1-naphthalenyl)-3-R-methyl-1-penten-3-olMANOOLNsc165961
Show more names
Manool (80%)(13R)-Labda-8(17),14-diene-13-ol[13R,(+)]-Labda-8(17),14-dien-13-ol[13R,(+)]-Labda-8(17),14-diene-13-ol4ARTRANS-5-(-TETRAME-2-METHYLENEDECAHYDR5-(5,5,8a-Trimethyl-2-methylenedecahydro-1-naphthalenyl)-3-methyl-1-penten-3-ol(αR,1S,4aS,8aS)-α-Ethenyldecahydro-α,5,5,8a-tetramethyl-2-methylene-1-napthalenepropanol
Properties
Computed structural properties
- XLogP
- 5.7
- Topological polar surface area
- 20.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 4
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 422
Physicochemical properties
- Melting point
- 49 · 49-52 °C(lit.)
- Boiling point
- 150 · 150-153 °C(Press: 0.3 Torr)
- Density
- 0.93 · 0.93±0.1 g/cm3(Predicted)
- Flash point
- 230 °F · >230 °F
- storage temp.
- 4 °C, · 4°C, stored under nitroge
- solubility
- Benzene (Slightly), Chloroform (Slightly), Methanol (Slightly)
- form
- Low-Melting Solid
- pka
- 14.47 · 14.47±0.29(Predicted)
- color
- White to Off-White
- Specific Gravity
- 0.97 · 0.97
- Odor
- Very delicate, woody, dry-sweet, and extremely tenacious odor
- LogP
- 6.79 · 6.790 (est)
- FDA UNII
- 5 PJ0PV00 · AT5PJ0PV00
- Symbol(GHS)
- 7 · GHS07,GHS09
- Signal word
- Warning
- Hazard statements
- 315 · H315-H400-H319-H335
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS09
- hazard_code
- Xi
- safety_code
- 26-36
- Hazard statements
- H315-H400-H319-H335
- REACH Registrations
- Active
- Precautionary statements
- P273-P391-P501-P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P
Chemistry & industry
Applications
UsesMaintains anti-proliferative activity against human malignant cell strains.
Preparation methods
PreparationBy extraction of cornrninuted wood of Dacrydium biforme, a tree indigenous to New Zealand, with alcohol or Acetone. The extract is neutralized with alkali, and the crude Manool may be recrystallized.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: A labdane diterpenoid in which the labdane skeleton has double bonds at positions 8(17) and 14 and carries an R-hydroxy group at position 13.
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Related reactions
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Compound notes
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