Resin Acids and Sterols

7/23/2019 Resin Acids and Sterols

1/20

PSE 406 Lecture 13 1

Wood Chemistry

Wood Chemistry

PSE 406/Chem E 470

Lecture 13

Diterpenes and Triterpenes


2/20


Wood Chemistry Pitch Chemicals

When you grab a softwood tree

and your hand sticks to the tree,

you have discovered pitch.

Pitch consists of about 5!5terpenes and resin acids. "esin

acids are g#assy #ike che$ica#s

a#so $ade of isoprene units.

The %hrist$as tree &'$ ho#ding

didn't have any pitch #eft.


3/20


Wood Chemistry Pitch as a Bandage

When a softwood tree

is wounded, it re#eases

pitch to (sea#) the

wound.* Terpenes serve as the

antiseptic and then

evaporate.

* "esin acids serve as thebandage +and a#so as an

antiseptic.


4/20


Wood Chemistry Rosin

The ter$ rosin refers to a $i-ture of resin acids

produced through the disti##ation of pitch.

u$ rosin/ disti##ation of gu$ resins +wound resin

* 0 12 $etric tons +1224 Ta## oi# rosin/ fro$ the wedish word ta##oa which

$eans pine oi#. Produced during the kraft pu#ping

process.

* 0 67, $etric tons +1224 Wood rosin/ Disti##ation of o#d stu$ps.

* 0 3, $etric tons +1224


5/20


Wood Chemistry Diterpenes: Strctre

7 isoprene units #inked head to tai#

8eutra#s/* 9ydrocarbons, pheno#ics, a#coho#s, ketones and a#dehydes

:cids/ Typica##y referred to as resin acids :cid content $uch higher in heartwood than sapwood

COOH

Abietic Acid

CH2OH

Pimarinol Pimaradiene

CHO

Levopimaral


6/20


Wood Chemistry Diterpenes: Strctre

"ing structures

*:cyc#ic, $ono, di, tri and tetracyc#ic

* ;acrocy#cic +1


7/20

PSE 406 Lecture 13 $

Wood Chemistry Diterpenes: !ocation in "ree

%o$position is very species dependent

;ain#y found in conifers +.6#eoresin/ ?= resin acids +tricyc#ic!%>>9

* 9eartwood/ Large a$ount of neutra# diterpenoids

that have been $odified through various reactions/@:ro$atiAation, hydro-y#ation, o-idation, B rearrange$ents

+often #osing % ato$

Tropica# 9ardwoods/* anda#wood/ 16


8/20

PSE 406 Lecture 13 %

Wood Chemistry

DiterpenesPhysical Properties

"osin +$i-ture of diterpenoids is g#ass #ike/ it s#ow#y

softens when heated @ does not have a $e#ting point

Pure resin acids are crysta##ine

* Pi$aric acid $p C 61


9/20

PSE 406 Lecture 13 &

Wood Chemistry

Diterpenes

Plp and Paper Pro#lems

To-icity

* Diterpenoids are pri$ary po##utants in pu#p $i##

eff#uents* Fery to-ic to fish

* Difficu#t to re$ove in treat$ent syste$s

* LD5not particu#ar#y high +abietic 14$g!kg

* &nha#ation prob#e$s in saw $i##s

tickies


10/20


Wood Chemistry $ses o% Diterpenes

"osin/ ;i-ture of

resin acids

* u$ "osin* Ta## >i# "osin

0ses of "osin

* Printing &nks, Paper

iAe, "ubber,

:dhesives,

;isce##aneous


11/20


Wood Chemistry

"riterpenes & SterolsChemical Composition

G isoprene units #inked headto tai#

;any are c#assified assteroids +sterane structure* Triterpenoids and stero#s have

sa$e synthetic pathway sothey shou#d not be separated

* Hoth start fro$ sEua#ene and

then branch off

riterpene' 6 ( 5C

S)ualene


12/20


Wood Chemistry


HO

*Sito'terol

OH

HO

Serratenediol

HO

C+ole'terol

,not in tree'-

S)ualeneHO

*Sito'terol

HO

CH3

Campe'terol


13/20


Wood Chemistry


Triterpenoids e-ist in three for$s* Iree for$

* Jsters of fatty acids

* #ycosides

%an contain a #arge variety of functiona# groups* %arbo-y#

* Jthers

* :cety#* :#coho#s

* Ketones


14/20


Wood Chemistry

"riterpenes& SterolsPhysical Properties

-sitosterol

%rysta##ine

* $p 17% o#ubi#ity

* >rganic so#vents/ ether, a#coho#s, etc

Hoi#ing Point* ;erck inde-/ no boi#ing point #isted. Iound in

ta## oi# pitch < does not disti##


15/20


Wood Chemistry

"riterpenes & SterolsRole in 'atre

tero#s are found in p#ants as both free stero#s, as

stero# esters +of fatty acids and as stero# g#ycosides

erve as co$ponents of $e$branes

* Work with phospo#ipids to create $e$branes which are

on#y per$eab#e to certain che$ica#s

tero# esters

* He#ieved to serve as transport agent to get stero#s fro$

site of biosynthesis to $e$brane

tero# g#ycosides


16/20


Wood Chemistry Sterol le(els in plants

Leve#s of stero#s variab#e depending on p#ant.* Hrocco#i/ 3.7g!kg

* Hanana/ .5g!kg

*:#fa#fa 6.1 g!kg

*:spen +wood/ 5 g!kg

Iree stero#s are found in vegetab#e oi#s.

* Peanut oi#/ 1


17/20

PSE 406 Lecture 13 1$

Wood Chemistry

"riterpenes & Sterols"ree )n%ormation

Iound in both hardwoods and softwoods

* 8ot a very #arge co$ponent in softwoods

*


18/20

PSE 406 Lecture 13 1%

Wood Chemistry

"riterpenes & SterolsPlp and Paper Pro#lems

tero# esters are difficu#t to saponify/ known as

nonsaponifiab#es

* o$e che$ica# conversions during pu#ping but $ost#y

stab#e.

* Large nu$ber of reactions during b#eaching

@ saponification

9ydrophobic nature of stero# esters cause the$ to be

a $aor pitch prob#e$ in paper$aking* ;aor co$ponents of pitch deposits


19/20

PSE 406 Lecture 13 1&

Wood Chemistry

Sterols %rom "reesBenecol *+,

Heneco#/ cho#estero# reducing product.* Known since 125s that vegetab#e stero#s can

reduce b#ood cho#estero#.@ 9igh #eve#s of stero#s can cause other prob#e$s

* 12s shown that p#ant stano#s were effective at#owering cho#estero# without negative effects.@ tano#s not fat so#ub#e so difficu#t to use.

@ Iinnish co$pany +"asio deve#oped a procedure in #ate124s ear#y 122s to produce stab#e fat so#ub#e stano#esters fro$ p#ant derived stero#s.


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Wood Chemistry

Sterols %rom "rees:Benecol *-,

itostano#* i$i#ar structure to

sitostero#

* aturated stero#

* Iound in 8ordic Pine

&n Heneco# the

sitostano# is in the for$

of a fatty acid ester.

HO

Resin Acids and Sterols

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