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

Description

TOTAROL, also known as (4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol, is a naturally occurring diterpene with potent antimicrobial properties.

Uses

Used in Antimicrobial Applications:
TOTAROL is used as an antimicrobial agent for its potent antimicrobial activity. It is effective against a wide range of microorganisms, making it a valuable compound in the development of new antimicrobial treatments and products.
Used in Pharmaceutical Industry:
TOTAROL is used as a pharmaceutical compound for its antimicrobial properties. It can be incorporated into various drug formulations to enhance their effectiveness against bacterial and fungal infections.
Used in Cosmetics Industry:
In the cosmetics industry, TOTAROL is used as an antimicrobial agent to help preserve products and prevent the growth of harmful microorganisms, ensuring the safety and efficacy of cosmetic products.
Used in Food Industry:
TOTAROL is used as a preservative in the food industry to inhibit the growth of bacteria and other microorganisms, thereby extending the shelf life of perishable products and maintaining their quality and safety.

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

• 51905-97-6 (4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-3-(4-nitro-phenylazo)-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-2-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 
• 1357018-93-9 C₃₅H₅₂N₂O₃ 
• 1357018-92-8 C₃₃H₄₇ClN₂O₂ 
• 1357018-91-7 C₃₃H₄₈N₂O₂ 
• 1357018-86-0 C₃₀H₄₃NO₂ 
• 1005348-41-3 C₄₀H₅₈O₂ 
• 84104-88-1 totara-8,11,13-triene-12,13-diol dibenzoate 
• 250720-35-5 13-(β-D-lactopyranosyloxy)totara-8,11,13-triene 
• 250720-31-1 13-(α-D-mannopyranosyloxy)totara-8,11,13-triene 
• 250720-31-1 13-(α-D-galactopyranosyloxy)totara-8,11,13-triene 
• 250720-31-1 13-(β-D-galactopyranosyloxy)totara-8,11,13-triene 
• 250720-31-1 13-(β-D-glucopyranosyloxy)totara-8,11,13-triene 

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.