Abietic acid - Moligand™, ≥75% , CAS No.514-10-3

CAS: 514-10-3 Cat. No.: A107217 Molecular Weight: 302.45 Beilstein Registry Number: 2221451 EC Number: 208-178-3

GRADE & PURITY Moligand™, ≥75%

Synonyms

(1R,4aR,4bR,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene-1-carboxylic acid | DTXCID202047 | Abietate | Tox21_112386 | Abietic acid, technical | RSWGJHLUYNHPMX-ONCXSQPRSA-N | BALS 3A | C32BF2BB-9F97-4AF5-8F5E-06BC0EA97

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

Overview

Starting material for natural product synthesis. Epoxidation with MCPBA.
Abietic acid is used as a precursor in the preparation of petrochemical curing agents. It is used in the synthesis of dehydroabietic acid derivatives, that exhibit antitumor, antimycotic, and antiviral activities. It can also be used as a starting material in the total synthesis of (-)-triptolide[8] and (+)-amberketal.

Specifications

Synonyms

(1R, 4aR, 4bR, 10aR)-1, 4a-dimethyl-7-(propan-2-yl)-1, 2, 3, 4, 4a, 4b, 5, 6, 10, 10a-decahydrophenanthrene-1-carboxylic acid | DTXCID202047 | Abietate | Tox21_112386 | Abietic acid, technical | RSWGJHLUYNHPMX-ONCXSQPRSA-N | BALS 3A | C32BF2BB-9F97-4AF5-8F5E-06BC0EA97

Specifications & Purity

Moligand™, ≥75%

Storage

Store at 2-8°C, Protected from light, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Purity

≥75%

Names and Identifiers

• Canonical Smiles: CC(C)C1=CC2=CCC3C(C2CC1)(CCCC3(C)C(=O)O)C
• IUPAC Name: (1R,4aR,4bR,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid
• InChIKey: RSWGJHLUYNHPMX-ONCXSQPRSA-N
• 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
• Isomeric SMILES: CC(C)C1=CC2=CC[C@@H]3[C@@]([C@H]2CC1)(CCC[C@@]3(C)C(=O)O)C
• WGK Germany: 3
• RTECS: TP8580000
• Molecular Weight: 302.45
• Beilstein: 2221451
• Reaxy-Rn: 1915575
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1915575&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Diterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Diterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Diterpenoids
• Alternative Parents: Hydrophenanthrenes Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Diterpenoid - Abietane diterpenoid - Phenanthrene - Hydrophenanthrene - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
• External Descriptors: Abietane diterpenoids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

RARA Tclin Retinoic acid receptor alpha (1324 Activities)

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VDR Tclin Vitamin D receptor (26531 Activities)

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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

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NR1H3 Tchem LXR-alpha (2891 Activities)

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Homo sapiens (32628 Activities)

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A498 (42825 Activities)

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ACHN (49357 Activities)

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CAKI-1 (44928 Activities)

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CCRF-CEM (65223 Activities)

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COLO 205 (50209 Activities)

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DLD-1 (17511 Activities)

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DMS-273 (14108 Activities)

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HL-60 (67320 Activities)

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HT-29 (80576 Activities)

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K562 (73714 Activities)

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KM12 (47707 Activities)

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LoVo (4724 Activities)

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M14 (47487 Activities)

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MOLT-4 (49676 Activities)

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OVCAR-3 (48710 Activities)

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OVCAR-4 (44535 Activities)

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OVCAR-5 (45555 Activities)

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OVCAR-8 (47708 Activities)

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PC-3 (62116 Activities)

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RPMI-8226 (44974 Activities)

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RXF 393 (41971 Activities)

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RXF 631 (11415 Activities)

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SF-295 (48000 Activities)

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SK-MEL-2 (46422 Activities)

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SK-MEL-28 (48833 Activities)

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SK-MEL-5 (47095 Activities)

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SK-OV-3 (52876 Activities)

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SN12C (47755 Activities)

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SNB-19 (46794 Activities)

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SNB-78 (14240 Activities)

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TK-10 (45540 Activities)

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U-251 (51189 Activities)

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UACC-257 (46019 Activities)

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UACC-62 (47335 Activities)

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UO-31 (46270 Activities)

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XF498 (12972 Activities)

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A549 (127892 Activities)

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EKVX (44102 Activities)

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NCI-H322M (45589 Activities)

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HCC 2998 (41480 Activities)

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HCT-116 (91556 Activities)

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HOP-18 (11577 Activities)

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HOP-92 (41141 Activities)

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NCI-H460 (60772 Activities)

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Associated Targets(non-human)

Ppard Peroxisome proliferator-activated receptor delta (358 Activities)

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Pseudomonas fluorescens (1630 Activities)

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Salmonella typhimurium (15756 Activities)

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Staphylococcus aureus (210822 Activities)

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Staphylococcus epidermidis (22802 Activities)

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Escherichia coli (133304 Activities)

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Aspergillus flavus (8875 Activities)

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Aspergillus niger (16508 Activities)

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Bacillus subtilis (32866 Activities)

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Cutibacterium acnes (887 Activities)

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Pichia kudriavzevii (7448 Activities)

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Aspergillus fumigatus (16427 Activities)

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Plasmodium falciparum (966862 Activities)

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Candida albicans (78123 Activities)

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Candida parapsilosis (8521 Activities)

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Candida tropicalis (8381 Activities)

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Mus musculus (284745 Activities)

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Human alphaherpesvirus 1 (11089 Activities)

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Streptococcus mitis (390 Activities)

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RAW264.7 (28094 Activities)

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Vero (26788 Activities)

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Aspergillus terreus (892 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Gloeophyllum trabeum (56 Activities)

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Pdk1 Pyruvate dehydrogenase kinase (250 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility in water: Insoluble Solubility in other solvents: Soluble in diluted NaOH solution Soluble in alcohol, benzene, chloroform, acetone, ether and carbon disulfide
• Sensitivity: moisture & air&Light sensitive
• Specific Rotation[α]: [α]20/D −85±10°, c = 1% in ethanol
• Melt Point(°C): 150-165 °C
• Molecular Weight: 302.500 g/mol
• XLogP3: 4.800
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 302.225 Da
• Monoisotopic Mass: 302.225 Da
• Topological Polar Surface Area: 37.300 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 542.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Ningning Tan, Yaohang Weng, Haijun Li, Bo Chen, Lan Zhao, Biao Huang, Beili Lu, Lirong Tang.  (2024)  Copper abietate/polyvinyl acetate composite film for enhanced humidity sensing in Chinese herbal medicine monitoring systems.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2024.136656]

2. Yuxi Lu, Lei Huang, Wen Chen.  (2024)  Probing the role of hydrophobic groups on the performance of fatty acid surfactants for hematite flotation.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2024.125674]

3. Jiaqi Liu, Chunning Chen, Jiaxin Lu, Yalei Wang, Jingtong Zhai, Hongkun Zhao, Nan Lu.  (2025)  Fabrication of paper-based SERS substrates for detecting trace MG molecules in complex samples.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2025.114586]

4. Huifang Liu, Jianmei Yao, Rongxiu Yin, Chiyu Ma, Lulu Li, Wen Yang, Zhiwei Lei.  (2025)  Antifungal mechanism of carvacrol and osthole can disrupt cell structure integrity and interfere with energy metabolism in Neopestalotiopsis ellipsospora.  Frontiers in Sustainable Food Systems,      [PMID:] [10.3389/fsufs.2025.1591966]

5. Yuchen Zhang, Gonghao Wang, Die Yang, Yongbo Ding, Yinxiu Zuo, Liang Shen.  (2025)  Bio-based self-stratifying waterborne coatings via silicone-induced phase separation for enhanced hardness and anti-graffiti performance.  PROGRESS IN ORGANIC COATINGS,      [PMID:] [10.1016/j.porgcoat.2025.109622]