511-15-9

Basic information

• Product Name: TOTAROL
• Synonyms: TOTAROL;14-Isopropylpodocarpa-8,11,13-trien-13-ol;2-Phenanthrenol, 4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-1-(1-methylethyl)-, (4bS-trans)-;Podocarpa-8,11,13-trien-13-ol, 14-isopropyl-;TOTAROL (B637832K176);trans-Totarol;4BS-TRANS-8,8-TRIMETHYL-4B,5,6,7,8,8A,9,10-OCTAHYDRO-1-ISOPROPYL-PHENANTHREN-2-OL;4BS TRANS,8,8-TRIMETHYL4B,5,6,7,8,8A,9,1
• CAS NO: 511-15-9
• Molecular Formula: C₂₀H₃₀O
• Molecular Weight: 286.45
• EINECS: 200-158-5
• Mol File: 511-15-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 128-132 °C(lit.)
• Boiling Point: 369.4 °C at 760 mmHg
• Flash Point: 166.585 °C
• Appearance: /
• Density: 0.988 g/cm³
• Vapor Pressure: 5.6E-06mmHg at 25°C
• Refractive Index: 1.529
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 10.90±0.60(Predicted)
• CAS DataBase Reference: TOTAROL(CAS DataBase Reference)
• NIST Chemistry Reference: TOTAROL(511-15-9)
• EPA Substance Registry System: TOTAROL(511-15-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 511-15-9(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 511-15-9 differently. You can refer to the following data:
1. (4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol is a naturally occurring diterpene that exhibits potent antimicrobial activity.
2. (4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol (>90%) is a naturally occurring diterpene that exhibits potent antimicrobial activity.

InChI:InChI=1/C20H30O/c1-13(2)18-14-7-10-17-19(3,4)11-6-12-20(17,5)15(14)8-9-16(18)21/h8-9,13,17,21H,6-7,10-12H2,1-5H3/t17?,20-/m1/s1

Upstream product

• 596-85-0 manool 

Downstream Products

• 15340-82-6 13-acetoxytotara-8,11,13-triene 
• 84104-89-2 12-nitrototara-8,11,13-trien-13-ol 
• 2539-02-8 (+)-podototarin 
• 250720-30-0 13-(2,2',3,3',4,6,6'-hepta-O-acetyl-β-D-lactopyranosyloxy)totara-8,11,13-triene 
• 250720-26-4 13-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)totara-8,11,13-triene 
• 250720-26-4 13-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)totara-8,11,13-triene 
• 250720-26-4 13-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)totara-8,11,13-triene 
• 250720-26-4 13-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyloxy)totara-8,11,13-triene 
• 15340-83-7 13-methoxy-totara-8,11,13-triene 
• 74-98-6 propane 
• 832-69-9 1-methylphenanthrene 
• 111589-12-9 2-hydroxy-8-methylphenanthrene 
• 1005348-41-3 C₄₀H₅₈O₂ 
• 1357018-86-0 C₃₀H₄₃NO₂ 

Relevant articles and documents

A short and efficient synthesis of (+)-totarol

A concise route to multigram quantities of the antibacterial diterpene (+)-totarol (1) is reported. (-)-Sclareol (2) was converted to the target compound 1 using either a six- or a seven-step sequence, while only three steps were required to access (+)-totarol ( 1) starting from (+)-manool (9) or (+)-13-epi-manool (10), respectively. A novel one-pot intramolecular aldol condensation/α-alkylation protocol served as the key operation for streamlining the syntheses of 1. ARKAT-USA, Inc.