Totarol

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Totarol is a widely used ingredient in cosmetics, personal care, and skincare formulations. Depending on its function, it may serve as a moisturizer, preservative, emulsifier, or active ingredient to enhance the overall effectiveness and performance of a product.

Totarol (Wikipedia)

Totarol is a naturally produced diterpene that is bioactive. It was first isolated by McDowell and Easterfield from the heartwood of Podocarpus totara, a conifer tree found in New Zealand. Podocarpus totara was investigated for unique molecules due to the tree's increased resistance to rotting. Recent studies have confirmed totarol's unique antimicrobial and therapeutic properties. Consequently, totarol is a candidate for a new source of drugs and has been the goal of numerous syntheses.

Totarol
Names
IUPAC name
14-(Propan-2-yl)podocarpa-8,11,13-trien-13-ol
Systematic IUPAC name
(4bS,8aS)-4b,8,8-Trimethyl-1-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-ol
Other names
(4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.151.658 Edit this at Wikidata
EC Number
  • 622-932-2
UNII
  • InChI=1S/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-, ☒N
  • 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+/m0/s1
    Key: ZRVDANDJSTYELM-FXAWDEMLBD
  • CC(C)C1=C(C=CC2=C1CC[C@@H]3[C@@]2(CCCC3(C)C)C)O
Properties
C20H30O
Molar mass 286.459 g·mol−1
Melting point 128 to 132 °C (262 to 270 °F; 401 to 405 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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New Zealand scientist Sir Thomas Hill Easterfield was the first person to discover totarol. Photo 1920.
Totarol powder
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