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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H26O3
Molecular Weight 314.4186
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 7-OXODEHYDROABIETIC ACID

SMILES

[H][C@@]12CC(=O)C3=C(C=CC(=C3)C(C)C)[C@@]1(C)CCC[C@@]2(C)C(O)=O

InChI

InChIKey=MSWJSDLNPCSSNW-MISYRCLQSA-N
InChI=1S/C20H26O3/c1-12(2)13-6-7-15-14(10-13)16(21)11-17-19(15,3)8-5-9-20(17,4)18(22)23/h6-7,10,12,17H,5,8-9,11H2,1-4H3,(H,22,23)/t17-,19-,20-/m1/s1

HIDE SMILES / InChI

Molecular Formula C20H26O3
Molecular Weight 314.4186
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

7-oxodehydroabietic acid, a resin acid found in both aerosol from soldering with rosin flux and in rosin solids. In a murine model, conjugation (haptenation) of resin acids to proteins is required to generate antibodies against rosin. Conjugation of L-lysine to 7-oxodehydroabietic acid was predicted, with a Schiff base (or imine) linkage formed between C-7 of the resin acid and a free amino group of lysine. Resin acids accumulate in the plasma membrane, a non-aqueous environment apparently conducive to conjugation of 7-oxodehydroabietic acid with lysine side chains of membrane proteins. The result would be dehydroabietic acid covalently bound to protein, which could lead to interaction with immune cells having resin acid specificity. The haptenation mechanism presented may be involved in allergic contact dermatitis and occupational asthma observed from exposure to resin acid solids and aerosols.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Conjugation of 7-oxodehydroabietic acid to lysine, a haptenation mechanism for an oxidized resin acid with dermal sensitizing properties.
1999 Mar
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:34:34 GMT 2023
Edited
by admin
on Fri Dec 15 18:34:34 GMT 2023
Record UNII
I8PNL8FLID
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
7-OXODEHYDROABIETIC ACID
Common Name English
PODOCARPA-8,11,13-TRIEN-15-OIC ACID, 13-ISOPROPYL-7-OXO-
Common Name English
Code System Code Type Description
PUBCHEM
29212
Created by admin on Fri Dec 15 18:34:34 GMT 2023 , Edited by admin on Fri Dec 15 18:34:34 GMT 2023
PRIMARY
CAS
18684-55-4
Created by admin on Fri Dec 15 18:34:34 GMT 2023 , Edited by admin on Fri Dec 15 18:34:34 GMT 2023
PRIMARY
EPA CompTox
DTXSID5075074
Created by admin on Fri Dec 15 18:34:34 GMT 2023 , Edited by admin on Fri Dec 15 18:34:34 GMT 2023
PRIMARY
FDA UNII
I8PNL8FLID
Created by admin on Fri Dec 15 18:34:34 GMT 2023 , Edited by admin on Fri Dec 15 18:34:34 GMT 2023
PRIMARY