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Sigma-Aldrich

Abietic acid

technical, ~75% (GC)

Synonym(s):

7,13-abietadien-18-oic acid, Abietate, L-Abietic acid, Rosin acid, Sylvic acid, sylvic acid

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About This Item

Empirical Formula (Hill Notation):
C20H30O2
CAS Number:
Molecular Weight:
302.45
Beilstein:
2221451
EC Number:
MDL number:
UNSPSC Code:
12352002
eCl@ss:
32150233
PubChem Substance ID:
NACRES:
NA.22
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grade

technical

Quality Level

Assay

~75% (GC)

form

solid

optical activity

[α]20/D −85±10°, c = 1% in ethanol

mp

139-142 °C (lit.)
150-165 °C

functional group

carboxylic acid

storage temp.

2-8°C

SMILES string

CC(C)C1=CC2=CC[C@@H]3[C@](C)(CCC[C@@]3(C)C(O)=O)[C@H]2CC1

InChI

1S/C20H30O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h7,12-13,16-17H,5-6,8-11H2,1-4H3,(H,21,22)/t16-,17+,19+,20+/m0/s1

InChI key

RSWGJHLUYNHPMX-ONCXSQPRSA-N

Gene Information

human ... TNF(7124)

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Application

Abietic acid can be used as a precursor in the preparation of:       
  • Epoxy and petrochemical curing agents.[1][2]
  •  Dehydroabietic acid derivatives as potential antitumor, antimycotic, and antiviral agents.[3][4]

It can also be used as a starting material in the total synthesis of:
  • (−)-triptonide and (−)-triptolide as potent antitumor and immunosuppressant agents[5]       
  • quinone (−)-12-deoxyroyleanone as antileishmanial agent[5]       
  • abietic acid-derived catechol (methyl 11,12-dihydroxyabietate-8,11,13-trien-18-oate, MDTO) as a potential antioxidant agent[6]

Other Notes

Starting material for natural product synthesis[7][8][9]; Epoxidation with MCPBA[10]

Pictograms

Exclamation markEnvironment

Signal Word

Warning

Hazard Statements

Hazard Classifications

Aquatic Acute 1 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

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Customers Also Viewed

Slide 1 of 1

1 of 1

S. Valverde et al.
Tetrahedron, 42, 573-573 (1986)
H. Okawara et al.
Tetrahedron Letters, 23, 1087-1087 (1982)
Rosin-based acid anhydrides as alternatives to petrochemical curing agents.
Liu X, et al.
Green Chemistry, 11(7), 1018-1025 (2009)
Cytotoxic, immunomodulatory, antimycotic, and antiviral activities of semisynthetic 14-hydroxyabietane derivatives and triptoquinone C-4 epimers
Zapata B, et al.
MedChemComm, 4(9), 1239-1246 (2013)
Regioselective routes towards 14-hydroxyabietane diterpenes. A formal synthesis of immunosuppressant (−)-triptolide from (+)-abietic acid.
Alvarez-Manzaneda E, et al.
Tetrahedron, 63(45), 11204-11212 (2007)

Questions

1–2 of 2 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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